LIVE WEBINAR | TUESDAY, JUNE 9 | 3PM EDT
The STR Tax Strategy
How high-income investors use short-term rentals to offset W-2 income (without REPS)
A live session for high W-2 earners with short-term rentals, or thinking about buying one. Nick Aiola and Sam Ortiz walk through the qualifying tests, the case law that defines them, and the cost segregation strategy that drives the size of the savings.
Can’t attend live? You’ll get the replay, slides, and full deliverable bundle.
Who this session is for
If you fit any of these, this session was built for you.
You own a short-term rental
And you're not sure if you actually qualify for the tax strategy you've heard about.
You're considering an STR purchase
The decisions you make before closing have the biggest impact on whether the strategy works.
You have a high W-2 income
Physician, executive, dual-income household. Your rental losses are probably sitting suspended on your return doing nothing.
What we'll cover
A practical, end-to-end walkthrough. Not a sales pitch. Real mechanics, real case law, real numbers.
- 1The two qualifying testsThe 7-day rule and material participation. Where most investors fall short, and the case law that defines the boundaries.
- 2The property manager trapWhy your management setup is probably the single biggest threat to the whole strategy, and the three setups that actually hold up.
- 3Cost segregation and bonus depreciationHow accelerated depreciation drives the size of the Year-1 loss. Plus what 2025’s restoration of 100% bonus depreciation means for buyers this year.
- 4A worked exampleA line-by-line breakdown of a realistic client profile, showing how the qualifying tests and the depreciation strategy to produce real federal tax savings.
- 5Live Q&AOpen Q&A at the end where you can ask Nick and Sam about your specific situation.
What you get with registration
- Live access to the session and Q&ATuesday, June 9 at 3pm EDT
- The full session replaySent within 48 hours. Watch on your schedule.
- The slide deckWorked example, case law citations, do’s and don’ts.
- The STR Qualification CalculatorEstimate your potential savings in about three minutes.
Your presenters
Ready to go deeper on the strategy?
Tuesday, June 9 at 3pm EDT. $99 includes the live session, replay, slides, and the STR Qualification Calculator.
THE SESSION BEGINS IN
See what clients say…
EXCELLENTBased on 49 reviews Posted on LauraTrustindex verifies that the original source of the review is Google. Smart. Responsive. Responsible. My kind of accounting firm.Posted on Jaron MinerTrustindex verifies that the original source of the review is Google. Aiola helps me meet my goals for tax returns. Good communication.Posted on Adriana Nicole RosalesTrustindex verifies that the original source of the review is Google. Thank you Nick and team for giving us sound advice and getting our taxes done each year.Posted on Jay MaldonadoTrustindex verifies that the original source of the review is Google. My wife and I have been working with Aiola CPA for over four years and have been consistently satisfied with their services. Nick and his team are organized, responsive, and provide clear guidance that keeps the filing process efficient and on track. They offer objective, well-considered advice and consistently position us for optimal tax outcomes—both for the current year and long-term planning. Over time, their process has become even more streamlined, making each filing cycle faster and less burdensome. A specific note on Chris Tile—he was outstanding this year. He handled the complexities of our cost segregation and 1031 exchange with a high level of detail and follow-through. His responsiveness on last-minute updates ensured everything was accurately reflected and positioned to our advantage. Thanks Guys!Posted on Anna KundelTrustindex verifies that the original source of the review is Google. This year the process was extremely smooth. Sometimes the taxes got quite complicated. Because I had complete access to my team by email, text and phone it made the process without stress.Posted on Benjamin AcheampongTrustindex verifies that the original source of the review is Google. Have been great working with Nick and his team for the past 4 years. Chris, has been great, always diligent, communicates effectively and responds quickly. He always makes the tax preparation process stress free. Highly recommend this amazing team for real estate investors!Posted on rolando riveraTrustindex verifies that the original source of the review is Google. Chris was very helpful, and explained everything very well. Would definitely recommend Aiola CPA to anyone.Posted on Brandon DurkinTrustindex verifies that the original source of the review is Google. We have been a client since 2021 and highly recommend Aiola CPA. Not only do they provide excellent consulting services but also make the tax preparation and filing process as streamlined, transparent, and simple as possible. Very happy with the services provided.Posted on Bill ReefTrustindex verifies that the original source of the review is Google. Nick is extremely knowledgeable and able to explain complex tax situations and strategies in a easy to digest form, flexing for any follow on questions. I highly recommend Nick and his staff if you are needing a strong CPA.
Want a CPA that works with you as a partner and not a vending machine?
I’ve had interactions with other CPA/accounting firms and just haven’t felt like I was working with a partner who had my best interests in mind. Always feeling like I was being nickel and dimed for any help may have needed.
I have to say, that I am pleasantly surprised. My experiences to date with Nick have been very satisfying. He’s been available, competent, and very helpful. I would highly recommend him and urge you to contact him for the services his firm provides.
Excellent work!
Excellent work! This is the first time I worked with Nick after getting referral and research. He helped me to amend my 2018 tax return (the mistake made re. property depreciation by my previous CPA) as a result of getting me more refunds. He is very knowledgeable and through, asked me to provide detail documents for his analysis. I am pleased for his work on 2019 tax return as well. Trustworthy and strongly recommended!
Nick Aiola, CPA
Nick has helped me tremendously to straighten out the mess made by a previous accountant. He is sharp, up to date, and provided sound financial advice in addition to the tax accounting. Well worth it for new clients. I would highly recommend him.
Trustworthy Business Advisor
Nick is more than a professional accountant, he is a trustworthy advisor. Financial information is personal, so I expect my business to be treated as such. Nick goes the extra mile to ensure his work is consistent, transparent, and efficient, all while treating your personal information with care and confidentiality. Nick will be an important, accountable asset for any financial decision you may make in the future.
Great Service
In my fifty years of engaging the services of CPA and tax consultants, Nick Aiola stands head and shoulders above them all in every respect. I recommend him without reservation!
Best CPA you will ever find……period!!
Nick is incredible. Honestly, of all my “team members”, no one comes close. I wish I could find a lawyer half as competent as Nick. He’s super nice, responsive and he knows his sh*t.
Brilliant Accountant
I have been using Nick’s professional accounting services for just over one year now and he has been nothing short of astounding. Whether servicing my business or personal taxes, he is extremely devoted and passionate about his work. Exceptionally knowledgeable and has made my tax return process effortless. Highly recommend for business and personal accounts.
Exceptional CPA
Nick is an exceptional CPA that I definitely recommend to any Real Estate Investor or Entrepreneur. After interviewing several CPAs, I selected Nick for his professionalism and ability to clearly articulate complicated accounting practices into laymen’s terms which allowed for a better understanding of tax strategy. Nick also invests in real estate himself and proved to be well versed in tax strategy unique to real estate investing.
Wonderful CPA!
Nick is professional, smart, and generous with his time. He is very knowledgeable about accounting and tax law and always happy to educate his clients and the community at large. He provided efficient service and I am very happy with his work. I will definitely use him again and would recommend him to anybody. 🙂
Honest
My company has used Nick for the last couple of years and Nick has been nothing but caring and honest with me since day one. He cares about my company and gives me advice on what needs to be done. He is always available for my questions or concerns. He also does my personal taxes as well. I would highly recommend him.
Excellent service, highly recommended
I was very lucky to happen across Nick when it was time for me to find a good, real estate-focused CPA. We just went through our first full tax year, and Nick did an excellent job of preparing me for my increasingly-complicated tax situation. He got our business returns and personal returns expertly done, and helped us through every step of the process. He is always a great communicator and very prompt in his responses, and makes himself available whenever we need him. We are very happy with his services, and look forward to many more successful tax years together!
Experienced and trusted advisor that I would highly recommend
I have been using Nick’s accounting services for several years now and I am more than satisfied with not only the quality of his work but also with his dedication to make sure that I understood everything he was doing and how it would affect me in both the long and short term. He is a very patient individual who clearly has a passion for what he does and truly looks out for his clients’ best interest. Communication is very important to me and so naturally I felt very comfortable with Nick during our meetings and especially when he extended the offer to call or text him at anytime if I had any questions. I am confident that I am in good hands and 110% recommend him and his services.
Great Service
Nick did a great job helping us out with our taxes for the year. We ran into an issue and he was able to resolve it without a problem. Very responsive and willing to help!

