My wife and I purchased a condo and plan to use it primarily for short term rentals and as a vacation property. We're looking to take advantage of the short-term rental loophole. I'm setting up our business checking account and need to know what tax classification would be most financially advantageous.
I 100% recommend you to speak to your CPA - if you do not have one yet get one before the purchase etc, youll need it for the cost seg portion. I would ask this question to him and not take advice from the peanut gallery.
I would definitely recommend connecting with a cpa and an attorney on this. It depends on your goals. I’ve seen too many clients mess this up without proper advice
I recommend finding a tax strategist/tax accountant who specializes in real estate taxation and is proactive instead of reactive when providing advice.
Working remotely with your accountant will expand your options.
I would also recommend looking for an accountant willing to work with you throughout the year. You want an accountant who can help you strategize and who is responsive when you want to know the consequences of the financial decisions you are making throughout the year.
Happy to answer any questions. Good luck.
Bill Hampton
404-482-3170
Hampton Tax and Financial Services, LLC.4.896 ReviewsContact usWebsiteView PageEdit signature0 VotesQuoteSteadilySponsoredNeed property and liability insurance for your rentals? BP Investors trust Steadily for great rates and tailored coverage for short and long-term rentals.Get a QuoteFulton Abraham Sanchez
Suspended LTR depreciation/losses often aren’t lost, they can carry forward and may be released when you sell, so the “can’t use it” point may be overstated.
Real estate sale taxes aren’t just 15–20% LTCG: depreciation recapture, possible 3.8% NIIT, and state tax can raise the effective rate.
A 1031 has strict deadlines (45 days identify / 180 days close); if you need more time, consider reverse 1031 or a more passive “parking” option like DSTs.
STRs can potentially offset W-2 income, but it’s more complex than “100 hours”—material participation rules and documentation matter.
Cost segregation can be powerful but only if the deal supports it; it accelerates depreciation and can affect future recapture.
Consolidating into fewer properties can reduce operational risk, but watch market/regulatory/insurance volatility.
Best next step: compare hold vs sell taxable vs 1031 with full tax/return components (recapture, NIIT, suspended losses, timing risk).
Always consult with a CPA who specializes in real estate. Location isn’t an issue as long as they’re accessible via video meetings, phone calls, text, or email.
1,236Votes |1,007 PostsReplied 2 days agoQuote from @Fulton Abraham Sanchez: Suspended LTR depreciation/losses often aren’t lost, they can carry forward and may be released when you sell, so the “can’t use it” point may be overstated.
Best next step: compare hold vs sell taxable vs 1031 with full tax/return components (recapture, NIIT, suspended losses, timing risk).
Two good points right here. The first is interesting - I currently have a ton of passive disallowed losses. One of my biggest fears is locking in these passive losses. From what I understand I can only use passive losses to offset passive gains - meaning stock/account dividends in the future. I can't deduct from my W2, I'm not a REP either.
How could I use these when I sell? It seemed like I would be stuck w/ the depreciation recapture (which wouldn't effect much since I haven't been able to take it) and capital gains/losses.
My wife and I purchased a condo and plan to use it primarily for short term rentals and as a vacation property. We're looking to take advantage of the short-term rental loophole. I'm setting up our business checking account and need to know what tax classification would be most financially advantageous.
Thank you.
Can you explain further what you mean about "tax classification?"
There are two approaches here. It sounds like you are owning it directly (which is not always recommended if you are trying to get some additional anonymity for asset protection). If you are owning it directly, and you live in a community property state, you can elect for the LLC tax status to be treated as disregarded instead of a partnership. This is advantageous if you do not want to have to file an extra tax return (Form 1065).
Just tax basics here but LLCs can hold any tax election/status (disregarded, partnership, S-Corp, and C-Corp) but the default elections will be based on how many members are in the LLC. The default for a single member is a disregarded tax election and for more than 1 member is a partnership.
If you are looking to get the short term loophole and holding it long term as as a short term rental under no circumstances would I suggest you choose an S Corp or C Corp election. Also -- Make sure to track ALL your hours in a log to meet the short term loophole rules and avoid any issues if there's an audit.
Since you mentioned it will be multimember LLC - it will default to a partnership status unless you live in a community property state as I explained above.
And yes, like everyone said, speak with a CPA to help you understand what is best for your personal tax strategy.
There are potential tax pitfalls for having a STR that is also used for personal use. You may be limited your overall losses, connect with a CPA who can inform you of the rules.
Hey Jeffrey, excited for you and this new journey into short-term rentals! Like others have mentioned, you’ll definitely want to connect with a CPA who specializes in real estate—they can help you navigate all of this and make sure everything is documented correctly. The right setup really depends on your goals and overall financial picture.
A lot of people get into short-term rentals for what’s often called the “real estate loophole.” In simple terms, this means that if you materially participate and keep the average stay at 7 days or less, you may be able to offset your W-2 income with any losses, this is where the real benefit comes in. Depending on your goals, you might also consider a cost segregation study, which can accelerate depreciation and give you more flexibility, but that’s something to discuss with your CPA.
As for entity structure, an LLC is usually best for protection, but tax-wise, it doesn't change much. We typically advise clients to avoid a multi-member LLC if possible, since that gets taxed as a partnership and can increase complexity. Just a bit of insight a lot of the time, people are actually asking S-Corp or LLC, but S Corps usually don't help here since there's no self-employment tax to avoid, depreciation can get trapped, and exits can get messy. We advise clients in most cases to keep rentals out of S Corps. Keeping your short-term rental in a single-member LLC often keeps losses flowing cleanly and maximizes your ability to offset W-2 income. But, I would definitely interview a few CPAs to make sure you are applying all of this correctly and not missing any opportunities. There are a lot of good ones on here.
Hi Jeffrey, while the optimal tax classification for your multi-member LLC (typically a Partnership or S-Corp election) should be discussed with a tax advisor based on your specific situation, don't overlook cost segregation as a critical component of your short-term rental strategy.
A comprehensive cost segregation study will allow you to significantly accelerate depreciation on personal property within your condo. These accelerated deductions are key to generating the substantial passive losses often needed to fully leverage the short-term rental loophole and potentially offset active income, assuming you meet material participation tests.
It's a foundational move for maximizing tax benefits in this space.