Skip to content
×
Pro Members Get
Full Access!
Get off the sidelines and take action in real estate investing with BiggerPockets Pro. Our comprehensive suite of tools and resources minimize mistakes, support informed decisions, and propel you to success.
Advanced networking features
Market and Deal Finder tools
Property analysis calculators
Landlord Command Center
ANNUAL Save 16%
$32.50 /mo
$390 billed annualy
MONTHLY
$39 /mo
billed monthly
7 day free trial. Cancel anytime

Let's keep in touch

Subscribe to our newsletter for timely insights and actionable tips on your real estate journey.

By signing up, you indicate that you agree to the BiggerPockets Terms & Conditions
×
Try Pro Features for Free
Start your 7 day free trial. Pick markets, find deals, analyze and manage properties.
Followed Discussions Followed Categories Followed People Followed Locations
All Forum Categories
All Forum Categories
Followed Discussions
Followed Categories
Followed People
Followed Locations
Market News & Data
General Info
Real Estate Strategies
Landlording & Rental Properties
Real Estate Professionals
Financial, Tax, & Legal
Real Estate Classifieds
Reviews & Feedback

All Forum Posts by: William C.

William C. has started 24 posts and replied 85 times.

Quote from @Basit Siddiqi:

I think the performance of the STR should come first before you look at the tax savings.

What if Property 1 is a 15% cash on cash return + 5% appreciation but the Cost segregation study mentions that only 20% of the property is eligible for bonus depreciation.

Property 2 might allow 30% of the property to be eligible for bonus depreciation but only have a 5% cash on cash return and 5% appreciation.

Yes, property 2 provides a higher tax benefit but property 1 would out perform property 2.


 Thanks for taking the time to comment. I agree with your approach. It is what guides us. Tax play is secondary, but still want to be informed on it pre-purchase.

Quote from @Michael Plaks:
Quote from @William C.:

Has anyone built a custom spread calculator with the intent of quickly analyzing deals for STR loophole & cost seg purposes? If yes, can you share? If no, can you help my brainstorm what one could look like?

My thoughts are:

Step 1: Input purchase price. Separate out land value v. structure value. Carrying just the structure value forward.

Step 2: Use an online estimator tool like KBKG to enter the details of the property. This will spit out out a bonus depreciation number. Carry that forward.

Step 3: Optional. If this an ADU property, calculate the square footage of the STR and compare that to the overall square footage of the purchase. Carry a portion forward.

Step 4: Custom part. Estimate taxable income for the year. Using STR loophole (if not REPS) how much would taxable income be reduced by? Estimating combined marginal tax rate (fed & state), get an estimate of overall tax dollars saved.

Output from this could help a person pass on properties that don't hit a personal threshold of benefit, or move forward with the ones that do. I realize this is an oversimplification. What feedback and edits do you have?


Every cost seg company offers free projections that basically do exactly what you describe. No effort required from you at all, they do everything.

And then you set your expectations, go a tax accountant and receive the shock of your life when you are informed that you get only a small portion of what you expected.

This is because it's not a straightforward deduction but only a potential deduction facing multiple potential limitations and pulling other strings that can swing the bottom line result wildly.

Do ask for those free cost seg projections, but do not count on the end result matching them

 Thank you for the reply. This inspires me to nag the cost seg study providers for more estimates. I tend to avoid that since my closing rate compared to number of deals analyzed is so low.

My thought with building a personal calculator is to address some of the overstated estimates I have received in the past. I attribute that to me not providing enough detail and also the desire to win your business. My thought is a personal calculator would tend to be more accurate.

Quote from @Jason Malabute:

Hey William — this is a great initiative, but I strongly recommend working with a tax professional instead of trying to DIY a spreadsheet for something this nuanced. The STR loophole, cost segregation, and depreciation calculations involve a lot of moving parts and it's easy to either overestimate the benefits or miss compliance issues that could trigger an audit. A good CPA who specializes in real estate can model this accurately, factor in your personal tax profile, and make sure the strategy actually holds up if ever questioned.

I fully agree. Thought with a novice calculator is quick analysis. Much like the calcs available on BP. I have a CPA, and cost seg engineer that I work with. Having them analyze many deals that do not fit, would be an unfair use of their time by me. If a deal passes the initial filters, then of course I would engage the pro's.

Has anyone built a custom spread calculator with the intent of quickly analyzing deals for STR loophole & cost seg purposes? If yes, can you share? If no, can you help my brainstorm what one could look like?

My thoughts are:

Step 1: Input purchase price. Separate out land value v. structure value. Carrying just the structure value forward.

Step 2: Use an online estimator tool like KBKG to enter the details of the property. This will spit out out a bonus depreciation number. Carry that forward.

Step 3: Optional. If this an ADU property, calculate the square footage of the STR and compare that to the overall square footage of the purchase. Carry a portion forward.

Step 4: Custom part. Estimate taxable income for the year. Using STR loophole (if not REPS) how much would taxable income be reduced by? Estimating combined marginal tax rate (fed & state), get an estimate of overall tax dollars saved.

Output from this could help a person pass on properties that don't hit a personal threshold of benefit, or move forward with the ones that do. I realize this is an oversimplification. What feedback and edits do you have?

Just an update as this potential deal is quickly falling apart. Sharing details here so others may learn.

Sellers of the prop. had been operating multiple STR's in unpermitted structures. Part of their sell is this is a multi-STR business. At some point a property line was moved to create an additional buildable lot. During that process the county noticed one of the unpermitted structures. They went through the permitting process with the county for one of the structures. Given the zoning and county rules, they had to sign a perpetual affidavit saying the structure could never be used as a STR. My understanding is the same would be imposed on a new owner.

So STR loophole approach would be eliminated for someone like me who is not REPS. Also, have uncovered county-level issues with the new lot that was created. County is saying it is not a legal, buildable lot since the property line move was done incorrectly. These could all end up with favorable outcomes, but until they do the value of this opportunity is greatly diminished.

Quote from @Michael Plaks:

@William C.

I personally would not be concerned about this structure's permit status for tax purposes. Our tax code tries to be blind to legal compliance outside of taxation. To give you an example, you're supposed to report your business income for tax purposes even if the source of income is illegal.

The most serous concern for me would be the one raised by @Chris Seveney: insurance. And with STRs, the risk of an insurance claim is higher.


This is good counter-point. Thanks for taking the time to respond. The insurance and risk piece is daunting. There is precedence in our area for being able to obtain insurance for an unpermitted STR. Each situation is unique and we would fully vet ours. For now, focused on if a cost seg, bonus depreciation, STR loophole approach would be viewed favorably or not. Thanks again.

Quote from @Chris Seveney:
Quote from @William C.:

Unique situation. I can provide more info as needed. Proposed strategy is to purchase a property that has both permitted and non-permitted, but livable, structures. Use one of the non-permitted structures as a STR (it's currently successfully being used this way by the owners). Do a cost seg on that non-permitted structure and use the STR loophole to utilize those losses for tax off-setting purposes. Any opinions on tax legality of this?


 Big Red Flag: For a cost segregation study, the asset must be depreciable under the IRS rules, and that typically means it must be a legal, capitalizable structure.

Typically, Non-permitted = Non-depreciable: If a structure wasn’t legally built or doesn’t meet code, it’s questionable whether it qualifies as an asset with a determinable useful life under IRS guidelines.

Also If the unit is illegal to rent (because it's unpermitted), you’re again treading into risky territory. Even if it’s "currently being rented successfully," that doesn’t make it compliant or safe from penalties if caught.

We will not even get into the liability and insurance component, but this is one way to get sued and be sued personally in a way insurance would not cover you.
Excellent feedback. Thank you.

Unique situation. I can provide more info as needed. Proposed strategy is to purchase a property that has both permitted and non-permitted, but livable, structures. Use one of the non-permitted structures as a STR (it's currently successfully being used this way by the owners). Do a cost seg on that non-permitted structure and use the STR loophole to utilize those losses for tax off-setting purposes. Any opinions on tax legality of this?

Quote from @Ashish Acharya:

@William C. If you and your spouse earn $300K in W-2 income and operate a short-term rental (STR) with average stays under 7 days, actively participate, and run a cost segregation study that creates a $60K loss, that loss can offset your W-2 income—even without qualifying for real estate professional status. This would reduce your taxable income to $240K. Assuming a combined federal and state tax rate of ~38%, you'd save around $22K–$24K in taxes—not the full $40K you currently pay. Any unused portion of the loss can carry forward to future years to offset STR or other non-passive income if material participation continues.

This post does not create a CPA-Client relationship. The information contained in this post is not to be relied upon. Readers should seek professional advice.

Great summary. Very helpful. Thank you.
1 2 3 4 5 6 7