🏨 Boutique Motel STR Loophole Hack - Is Depreciation Possible if Owner Operated?

Question

Here's a hack you won't find on social media (maybe because it's wrong): Converting a boutique hotel to STRs. NOTE: This post is intended for input from CPAs and Tax PROS as I would like to verify some details as have some relevant properties coming to market..

I've written about boutique motels/hotels being the next forefront for STR investors and operators. With most densely saturated and populated areas tightening nightly rental rules & regulations - an area of growing emphasis will be cottage cluster boutique motel/hotels (often at $100K-) per unit that are zoned and intended for high-density usages.

Many smaller (sub 10-15 keys) owner or self-operated boutique motels or hotels are just that - operated the by the same team and the same way for eons. The units are often not on AirBNB or branded (from this century) and in many cases the complete opposite of AirBNB's. There are often managers living on site and a desk check in. In most tourist areas I travel - there are examples of properties that have been transitioned and re-invested, re-branded, designed and essentially converted into individual listings on AirBNB and generally perform well. Think of it like a micro STR portfolio but the units are all on the same property..

The angle I propose is:  provided the new owner operator does not have on site manager (remote?) and the primary participator is the investor or spouse (guests, pricing, cleaning, marketing) and operated more like a cluster of STRs than a larger hospitality business AND with stays that average less than 7 days...accelerated depreciation is possible? Per Google - you could perform a cost segregation study that separates the different property components and then take the bonus depreciation?

If that is the case - this is further confirmation that this asset class is currently overlooked for experienced vacation rental investors and primed for growth.

Commercial lending is often not as difficult (although more involved) as investors anticipate. Depending on the scale and location of the property, many local credit unions or even the seller themselves will offer terms with 25-35-50% down (depending on the cash flow) and even higher LTV's with well qualified buyers on SBA or business loans.

Any TAX related insight into this theoretical strategy is greatly appreciated! THX.

Craig Jones · Answer

We did exactly this last year. Bought a former bed & breakfast in a popular tourist spot which is essentially a 5-room motel with a manager’s unit. Except the “manager’s unit” is really a 3000 sqft SFR tacked onto the side of the motel — which we occupy as our primary residence.

We put keycode locks on all the guest room doors and turned it into a self-service motel/STR hybrid. 50% direct bookings on our own website and the other half is a pretty even mix of Expedia, Booking.com and AirBnB. 82% occupancy our first 12 months.

The property is owned by our S-corp and we live onsite in the employer-provided housing as a condition of our employment as managers. The logic is a little circular since we are both employer and employees but this framing allowed us to include the entire property in the cost seg and bonus depreciation, which our CPA signed off on. The housing benefit is also non-taxable as income because onsite residence is an employment requirement.

The property’s cash flow is just okay on its own but when you consider that it also zeroes out our personal housing expense it looks pretty stellar.

Andrew Steffens · Answer

Good idea/questions.  Ill add another - I have had an influx of house hacker clients where they live in one unit and STR the rest.  Can they qualify for accelerated/bonus depreciation if it is also their primary residence?

Josh Lewer · Answer

@AJ Wong I like the idea, but a boutique hotel is already an active trade or business because it provides substantial services such as daily cleaning and concierge. That means cost segregation and bonus depreciation are already available, and those deductions can offset other income if the owner materially participates (already similar to the "STR loophole"). Converting to a true STR model that eliminates hotel-style services does not create new depreciation benefits. The real change is tax characterization: a hotel-style operation is typically reported on Schedule C and can be subject to self-employment tax, while a true STR without substantial services is usually reported on Schedule E and is not subject to self-employment tax. In both cases, to use losses against other income, the owner still needs to meet a material participation test.

Josh Lewer · Answer

@Andrew Steffens I like it but one note I’d make sure the losses aren’t limited by personal use days, which can get tricky when the owner lives on-site. It sounds like @Craig Jones has a solid setup with clearly separated units, keycodes, and locks, which helps keep the activity clean from a tax standpoint. It’s also important to confirm that there’s actually an appetite for the tax benefit; this strategy tends to make the most sense once you’re in a higher / highest tax bracket. And remember, the accelerated depreciation benefit is mainly a timing advantage: you’re pulling future deductions into the first year rather than creating a permanent savings.

Good thread.

Craig Jones · Answer

Just want to point out that timing has a quantifiable monetary value. I.e. deferring $100K of tax in year 1 is worth more than deferring $2564 annually over 39 years due to the time value of money. You can use a present value / future value formula to calculate that number.

Also, if you are a long term buy and hold type of investor and expect to pass real estate to your heirs, they will receive a step-up in basis. Which resets the depreciation schedule and wipes out any recapture.

Aaron Zimmerman · Answer

@Josh Lewer great synopsis and as a fellow cpa I agree with your analysis here.

AJ Wong · Answer

This is GREAT. Thank you! We help roughly 10-15 STR investors per year and have a hard time with Cost Seg and RE specific CPAs references throughout Oregon..any chance we can connect sometime? Thanks!!

Ashish Acharya · Answer

@AJ Wong

You’re thinking about it the right way. If you run the property like a group of short-term rentals, average stay under 7 days, no full-time on-site manager, and you or your spouse handle guest communication, pricing, and operations, it can qualify as an active trade or business instead of a passive rental.

That’s important because it lets you use cost segregation and take bonus depreciation, just like on regular STRs. The key is proving you materially participate, meaning you’re actually managing it day to day. Keep logs of your time spent on bookings, cleaning coordination, and maintenance.

If you do that, yes, converting a small boutique hotel into STR units can be a powerful tax play with big upfront write-offs.

Josh Lewer · Answer

@AJ Wong would be glad to!

AJ Wong · Answer

THIS is what I'm talking about! Amazing. Have seen a few 'conversions' on the Oregon Coast that have done exceptionally well with this strategy. Just listed a 12 unit with a mangers unit that would make a great 13th!

🏨 Boutique Motel STR Loophole Hack - Is Depreciation Possible if Owner Operated?

Most Popular Reply