Opening Note

You’re reading the latest issue of Death, Taxes, and Depreciation.

It’s a question that comes up more than you’d think, especially after a significant acquisition or a busy filing season: what happens if you didn’t claim bonus depreciation when you should have?

The answer is more nuanced than a simple yes or no. Whether you’re dealing with a prior-year miss or thinking through whether to claim it at all, the mechanics here are worth understanding before your next filing decision.

Missed Bonus Depreciation: Your Options and What the IRS Actually Allows

The instinct is usually to amend the return. But in most cases, that’s not the necessary move.

The IRS-preferred path for catching up on missed depreciation is Form 3115, Application for Change in Accounting Method. This approach, known as a Section 481(a) adjustment, lets you recover missed depreciation without filing amended returns for multiple prior years.

There are limited cases where an amended return is the right path. Specifically, if bonus depreciation was never properly elected out and you want to apply it retroactively, and you’re still within the three-year window from the original due date of the return. But that’s the exception, not the rule.

One thing worth flagging: electing out of bonus depreciation isn’t optional or informal. The IRS requires an affirmative election out, attached to a timely filed return for the year the property was placed in service, identifying the property class and citing IRC Section 168(k)(7). If that election isn’t made, the IRS treats you as taking bonus depreciation by default. Missing the window can create a tax position that’s difficult or impossible to unwind.

Why someone would elect out in the first place

This surprises some people, but there are legitimate strategic reasons to skip bonus depreciation even when you qualify for it:

• You’re already in a loss position and additional deductions don’t help you this year

• State tax law doesn’t conform to federal bonus depreciation, creating reporting complexity

• You’d rather spread deductions across years to offset income when tax rates are higher

• Passive activity loss limitations would suspend the losses anyway

The decision shouldn’t be made in isolation. It depends on your entity structure, your income profile across years, and how the numbers interact with your broader tax position.

The combination that matters most

When bonus depreciation is available and the timing is right, pairing it with a cost segregation study is where the real leverage comes from. Reclassifying building components into shorter-life asset categories increases the portion of a property eligible for bonus depreciation. That combination can generate deductions that meaningfully change cash flow in the year of acquisition.

The flip side is that complexity goes up. Missed elections, improper classifications, and unclaimed depreciation all carry risk. Getting the mechanics right from the start is easier than correcting them later.

Upcoming Events & Important Deadlines

Next Live Webinar:

Topic: Calculating the R&D Tax Credit: How the Credit Is Calculated and Claimed on Form 6765

Date & Time: Tuesday, June 9 @ 1:00 PM (Central)

Who it’s for: CPAs, Advisors

Register here: Registration Link

CPE credit available

Deadlines:

• June 16 - Q2 estimated tax payments due

Partnership Opportunity

Know someone who could benefit from cost segregation or related tax strategies?

We work closely with CPAs, advisors, and real estate professionals to help their clients uncover tax savings through cost segregation and complementary services.

If you’re interested in learning more about our partnership program, we’d love to connect.

(you can reply directly to this newsletter)

Other Announcements

We’ve recently partnered with MakeItDeductible.ai to give our subscribers access to their enhanced documentation service for STR, REPS, and equipment investors. If you have significant deductions tied to active participation, we suggest trying it. Your first 5 reports are free, with no commitment.

MakeItDeductible.ai is a white-glove, human-supported service built by a former CPA with 30+ years of experience in evidence documentation. For each qualifying task or event, simply send a quick note (what you did, how long it took, and any photos). A dedicated team reviews every entry, coaches you on best practices, and answers questions - then turns it into IRS-defensible documentation and provides a quarterly Excel summary for you and your CPA.

How it works: 1. Send a quick note, 2. Get a CPA-ready report, 3. Get a quarterly and annual summary

How to get started:

• Send a WhatsApp message to +1 (770) 313-3821 or email MakeItDeductible@guided101.com

• Include [RON300] to lock in the exclusive 5 free reports offer

Follow us on X: @DeathTaxesDep

Opening Note

You’re reading the latest issue of Death, Taxes, and Depreciation.

April 15 is behind us. For most CPAs and advisors, the last few weeks looked a lot like triage - extensions filed, returns wrapped up, and a string of conversations that probably should have started in January.

One question kept coming up in those late-inning calls from clients: what is actually the difference between an engineering-based cost segregation study and the DIY options that have been gaining traction?

Engineering-Based vs. DIY Cost Segregation: The Difference That Shows Up at Audit

Cost segregation works by reclassifying building components into shorter depreciation categories. Instead of depreciating everything over 39 years, qualifying assets get moved to 5-, 7-, or 15-year schedules. That acceleration unlocks real cash flow, often in year one. The strategy isn’t new, and with 100% bonus depreciation now permanent under the One Big Beautiful Bill Act, the stakes around getting it right have gone up considerably.

The question isn’t whether to do a cost segregation study. For most commercial property owners, the answer is yes. The question is how.

On accuracy: Engineering-based studies are conducted by teams with backgrounds in construction, engineering, and tax law. They go component by component - electrical systems, plumbing, flooring, landscaping, HVAC - and apply technical judgment at each step. DIY approaches work from templates and software tools that generalize where precision is required. The result is usually a study that misses reclassifiable assets, which means leaving money on the table, or one that overstates positions that can’t be supported.

On audit risk: The IRS has published specific guidance on what a defensible cost segregation study looks like. Engineering-based studies are built to meet that standard - detailed documentation, clear methodology, traceable calculations. DIY studies frequently fall short on substantiation. When deductions get disallowed, the savings disappear and penalties can follow. The lower upfront cost of a DIY approach does not account for that downside.

On the expertise gap: A cost segregation study done right requires multidisciplinary knowledge that most property owners and their accountants simply don’t have - and shouldn’t be expected to have. Missing a qualifying asset isn’t a mistake; it’s just a function of what the work actually requires to do well.

The practical takeaway for advisors: if clients are asking about cost segregation now, the opportunity is still there. Studies can be applied retroactively. But how it gets done determines whether the benefit holds. An engineering-based study is a defensible, documentable asset. A poorly supported DIY attempt is a liability that may not surface until years later.

Upcoming Events & Important Deadlines

Next Live Webinars:

1. The OBBBA Playbook: R&D Tax Credits and Cost Segregation Strategies Every Wealth Manager Should Know

   1. Date & Time: Wednesday, May 6 @ 11:00 AM CST

   2. Who it’s for: Wealth Managers, CPAs, Investors

   3. Register here: Registration Link

2. Active or Passive? Tax Strategies for Active and Passive Real Estate Investors

   1. Date & Time: Thursday, May 13 @ 12:00 PM (Central)

   2. Who it’s for: CPAs, Advisors

   3. Register here: Registration Link

   4. CPE Credit Available

Deadlines:

• May 15 - Extended Partnership & S-Corp returns (if on extension)

• June 15 - Q2 estimated tax payments due

• June 30 - Section 179D construction start cutoff

Partnership Opportunity

Know someone who could benefit from cost segregation or related tax strategies?

We work closely with CPAs, advisors, and real estate professionals to help their clients uncover tax savings through cost segregation and complementary services.

If you’re interested in learning more about our partnership program, we’d love to connect.

(you can reply directly to this newsletter)

Other Announcements

We’ve recently partnered with MakeItDeductible.ai to give our subscribers access to their enhanced documentation service for STR, REPS, and equipment investors. If you have significant deductions tied to active participation, we suggest trying it. Your first 5 reports are free, with no commitment.

MakeItDeductible.ai is a white-glove, human-supported service built by a former CPA with 30+ years of experience in evidence documentation. For each qualifying task or event, simply send a quick note (what you did, how long it took, and any photos). A dedicated team reviews every entry, coaches you on best practices, and answers questions - then turns it into IRS-defensible documentation and provides a quarterly Excel summary for you and your CPA.

How it works: 1. Send a quick note, 2. Get a CPA-ready report, 3. Get a quarterly and annual summary

How to get started:

• Send a WhatsApp message to +1 (770) 313-3821 or email MakeItDeductible@guided101.com
• Include [RON300] to lock in the exclusive 5 free reports offer

Follow us on X: @DeathTaxesDep

Subscribe now

Opening Note

You’re reading the latest issue of Death, Taxes, and Depreciation.

The Senate just passed the largest housing bill in decades. Most of the coverage has focused on the political angle - Wall Street versus Main Street, institutional investors versus individual homebuyers. But that framing misses the more interesting conversation.

For real estate investors, advisors, and CPAs, the relevant question isn’t who passed what. It’s how a shift in federal housing policy changes the planning calculus - on acquisitions, hold periods, exit timing, and the tax strategies tied to all of it.

The Senate’s Housing Bill: What It Says and What It Means for Investors

The 21st Century ROAD to Housing Act passed the Senate on March 12, 2026, by a vote of 89 to 10. It was co-authored by Sen. Tim Scott (R-SC) and Sen. Elizabeth Warren (D-MA) - about as bipartisan as legislation gets right now, which reflects how much political pressure exists around housing affordability heading into the midterms.

The bill still needs House approval. A narrower version already passed there, so reconciliation is the likely next step. Nothing is law yet, but the direction is clear enough to start thinking through the implications.

What’s Actually in the Bill

The legislation contains roughly 40 provisions aimed at increasing housing supply and lowering costs.

On the supply side, it targets regulatory barriers at the local level, encouraging governments to expand housing development and reduce friction around construction approvals. It also expands manufactured housing by eliminating the permanent chassis requirement, a change that could reduce per-unit costs by $5,000 to $10,000. In markets where construction economics are already tight, that matters.

On the financing side, the bill makes it easier for homeowners and landlords to get loans for home repairs, aimed at addressing the aging existing housing stock.

The provision drawing the most attention is the institutional investor cap. Once a firm owns 350 single-family homes, they’re blocked from purchasing more existing inventory. New construction and rehab are still permitted - but that carve-out comes with a catch.

The Build-to-Rent Wrinkle

Large investors who build or own single-family rentals would be required to sell after seven years, with a three-year extension if the renter wants to stay. Several House Republicans have pushed back, arguing this discourages new rental construction at a time when supply is already the core problem. That fight will play out in reconciliation.

But if the provision survives, it creates a planning problem that needs to be modeled from day one. A forced sale at a defined point in time changes the tax math considerably. Any strategy that front-loads depreciation deductions has to account for the recapture exposure at exit. The two can’t be treated separately.

What This Means for Your Planning

A few things worth working through before this reaches its final form.

Hold period assumptions drive downstream decisions - entity structure, depreciation approach, financing terms. If you’re underwriting BTR deals with an open-ended hold, that assumption may need revisiting.

Manufactured housing is worth a closer look. Lower per-unit costs, broader financing access, and an expanded legal definition could make factory-built rentals a competitive option in markets where traditional construction hasn’t been penciling.

And if institutional capital steps back from existing single-family inventory, pricing in certain submarkets could soften. Deals that weren’t working before might start to.

Upcoming Events & Important Deadlines

Next Live Webinar:

Topic: Repair Regulations: How to Expense Repairs and Maximize Deductions
Date & Time: Wednesday, April 29 @ 11:30 AM (Cen)
Who it’s for: CPAs / Advisors / Real Estate Investors

Register here: Registration Link
CPE credit available

Deadlines:

• April 15 – Individual & C-Corp tax filing deadline (or extension); Q1 estimated tax payments due

Partnership Opportunity

Know someone who could benefit from cost segregation or related tax strategies?

We work closely with CPAs, advisors, and real estate professionals to help their clients uncover tax savings through cost segregation and complementary services.

If you’re interested in learning more about our partnership program, we’d love to connect.

(you can reply directly to this newsletter)

Other Announcements

We’ve recently partnered with MakeItDeductible.ai to give our subscribers access to their enhanced documentation service for STR, REPS, and equipment investors. If you have significant deductions tied to active participation, we suggest trying it. Your first 5 reports are free, with no commitment.

MakeItDeductible.ai is a white-glove, human-supported service built by a former CPA with 30+ years of experience in evidence documentation. For each qualifying task or event, simply send a quick note (what you did, how long it took, and any photos). A dedicated team reviews every entry, coaches you on best practices, and answers questions - then turns it into IRS-defensible documentation and provides a quarterly Excel summary for you and your CPA.

How it works: 1. Send a quick note, 2. Get a CPA-ready report, 3. Get a quarterly and annual summary

How to get started:

• Send a WhatsApp message to +1 (770) 313-3821 or email MakeItDeductible@guided101.com
• Include [RON300] to lock in the exclusive 5 free reports offer

Follow us on X: @DeathTaxesDep

Subscribe now

Opening Note

You’re reading the latest issue of Death, Taxes, and Depreciation.

As filing deadlines approach, most conversations this time of year center around compliance. Getting returns finalized. Hitting the deadlines. Checking boxes.

But the bigger opportunity isn’t just filing correctly. It’s really all about planning strategically.

One theme that keeps surfacing in conversations with CPAs and investors is that many businesses are still treating tax credits and deductions as reactive tools rather than proactive strategy.

This month, we’re stepping back from individual provisions and looking at the broader framework: how to layer credits, deductions, structure, and timing into a coordinated strategy that improves cash flow and long-term growth.

Building a Strategic Tax Stack: Credits, Deductions & Timing

One of the biggest misconceptions we see is using the terms tax credits and tax deductions interchangeably. They are not the same.

• Tax deductions reduce taxable income. Think operating expenses, depreciation, retirement contributions.
• Tax credits reduce tax liability dollar-for-dollar. A $10,000 credit lowers your tax bill by $10,000.

Both matter. But credits often deliver more immediate impact, while deductions can create long-term planning flexibility.

Understanding the difference changes how you plan.

Key Opportunities We’re Seeing in 2026 Planning

• R&D Tax Credit – rewarding businesses investing in innovation and process improvement.
• Section 179D – deductions up to $5.81 per square foot for qualifying energy-efficient building improvements.
• Cost Segregation Studies – accelerating depreciation on building components to unlock upfront cash flow.
• 100% Bonus Depreciation – fully expensing qualifying assets placed in service.
• Work Opportunity Tax Credit (WOTC) – credits for hiring from targeted groups.

Structure and Timing Matter More Than Most Realize

Your entity type (S-Corp, C-Corp, partnership, LLC) affects how these benefits flow through and how savings are reinvested.

Timing can also be just as powerful:

• Deferring income into a lower-tax year.
• Accelerating deductions through cost segregation or bonus depreciation.
• Coordinating capital gains with losses.

The goal isn’t just minimizing this year’s tax bill.

It’s building a multi-year strategy that strengthens cash flow, improves after-tax returns, and positions the business for future growth or transition.

Proactive planning requires coordination. Make sure you’re working closely with your CPA and tax advisors now to ensure these strategies are evaluated before year-end decisions are locked in.

Upcoming Events & Important Deadlines

Next Live Webinar:

Topic: Section 179D and How to Retroactively Capture Deductions Via 3115
Date & Time: Wednesday March 18th, 12:00 pm CST
Who it’s for: CPAs / Advisors / Real Estate Investors

Register here: Registration Link
CPE credit available

Deadlines:

• March 15 – Partnership & S-Corp tax filing deadline (or extension)

• April 15 – Individual & C-Corp tax filing deadline (or extension); Q1 estimated tax payments due

Partnership Opportunity

Know someone who could benefit from cost segregation or related tax strategies?

We work closely with CPAs, advisors, and real estate professionals to help their clients uncover tax savings through cost segregation and complementary services.

If you’re interested in learning more about our partnership program, we’d love to connect.

(you can reply directly to this newsletter)

Other Announcements

We’ve recently partnered with MakeItDeductible.ai to give our subscribers access to their enhanced documentation service for STR, REPS, and equipment investors. If you have significant deductions tied to active participation, we suggest trying it. Your first 5 reports are free, with no commitment.

MakeItDeductible.ai is a white-glove, human-supported service built by a former CPA with 30+ years of experience in evidence documentation. For each qualifying task or event, simply send a quick note (what you did, how long it took, and any photos). A dedicated team reviews every entry, coaches you on best practices, and answers questions - then turns it into IRS-defensible documentation and provides a quarterly Excel summary for you and your CPA.

How it works: 1. Send a quick note, 2. Get a CPA-ready report, 3. Get a quarterly and annual summary

How to get started:

• Send a WhatsApp message to +1 (770) 313-3821 or email MakeItDeductible@guided101.com
• Include [RON300] to lock in the exclusive 5 free reports offer

Follow us on X: @DeathTaxesDep

Opening Note

You’re reading the first issue of Death, Taxes, and Depreciation.

We wanted a way to share what we’re seeing in the market, flag changes that matter, and keep the conversation going with the advisors and investors we work with. That’s it!

Heading into 2026, there’s a lot happening on the tax front. March 15 is right around the corner for S-corp and partnership returns, with individual filings due April 15. And beyond the usual deadlines, there are a couple of important dates to keep on your radar this year: June 30 for the Section 179D construction start cutoff, and July 4 for the R&D expense retroactive election for qualifying small businesses.

We’ll start with one of the bigger developments: the return of 100% bonus depreciation, and a nuance around timing that’s worth a closer look.

What’s changing in the industry and why it matters

100% Bonus Depreciation Is Still here, and It’s Permanent

The One Big Beautiful Bill Act passed in July 2025 restored full 100% bonus depreciation for qualifying property acquired after January 19, 2025. And this time, it’s here to stay. No more phase outs & watching the percentage tick down year after year.

This covers tangible personal property with recovery periods of 20 years or less, land improvements like parking lots and landscaping, and Qualified Improvement Property (think interior work like flooring, lighting, HVAC components).

Why this matters:

The permanence is a big deal. There’s no phase-out to plan around anymore, which gives investors and advisors a lot more flexibility when structuring deals and timing acquisitions.

A timing nuance worth noting:

This has come up in a few client conversations recently. There’s an assumption floating around that since 100% bonus depreciation is “back,” it applies to everything acquired in 2025 or even before. Not quite.

January 19, 2025 is the line. Property placed in service on or before that date? Still subject to the old phase-out rules as outlined in the previous legislation. Only property placed in service after that date gets the full 100%.

Upcoming Events & Important Deadlines

Next Live Webinar:

Topic: R&D and the OBBBA: Important Updates for 2026 and New Filing Requirements
Date & Time: Wednesday, February 11 @11:30 AM (Central)
Who it’s for: CPAs / Advisors / Real Estate Investors

Register here: Registration Link
CPE credit available

Deadlines:

• March 15 – Partnership & S-Corp tax filing deadline (or extension)

• April 15 – Individual & C-Corp tax filing deadline (or extension); Q1 estimated tax payments due

Partnership Opportunity

Know someone who could benefit from cost segregation or related tax strategies?

We work closely with CPAs, advisors, and real estate professionals to help their clients uncover tax savings through cost segregation and complementary services.

If you’re interested in learning more about our partnership program, we’d love to connect.

(you can reply directly to this newsletter)

Other Announcements

We’ve recently partnered with MakeItDeductible.ai to give our subscribers early access to their beta product.

MakeItDeductible.ai is a simple documentation tool that turns quick text messages, photos, and activity notes into CPA-ready, IRS-defensible records. You send a message describing an activity (or upload a photo), and the platform structures it into organized, time-stamped documentation aligned with business purpose and tax requirements, making it easier for you and your CPA to support deductions with confidence.

As part of this partnership, receive up to 5 documented events for free during the beta.

How to get started:

• Send a WhatsApp message to 770-313-3821

• Include [RON300] plus one activity you want documented

Follow us on X: @DeathTaxesDep

This newsletter serves two purposes:

1. To help property owners reduce taxes legally and aggressively through proven depreciation strategies

2. To keep CPAs in our network informed on upcoming events, tax updates, and planning opportunities affecting their clients

What You’ll Get Each Month

You can expect:

• Real-world cost segregation case studies with actual numbers

• Tax law updates impacting depreciation and real estate investors

• Engineering-based tax strategies

• Invitations to upcoming CPA-focused webinars, CPE events, and live trainings

• Actionable insights CPAs can immediately bring to their clients

Just relevant, high-quality information from professionals working in this space every day.

Who This Newsletter Is For

This newsletter is built for:

• Real estate investors

• Business owners

• High-income professionals seeking advanced tax planning strategies

• CPAs

• Advisors who want to stay ahead of accelerated depreciation strategies

Why We Created It

We created Death, Taxes, and Depreciation with a long-term vision: to build a trusted community of real estate investors, business owners, CPAs, and advisors who believe better information leads to better outcomes.

When depreciation and advanced tax strategies are understood and implemented correctly, they can do far more than lower a tax bill. They can:

• Unlock meaningful, repeatable cash flow

• Create flexibility and confidence in long-term planning

• Encourage smarter reinvestment decisions

• Strengthen collaboration between investors, CPAs, and engineers

This newsletter exists to bring everyone to the same table — owners and advisors alike — equipped with clear insights, real-world examples, and a shared understanding of the tools shaping real estate and business tax strategy today.

It’s a win-win for all!

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