New Investor - Trying to Slash Tax Burden

Member since 2025 · 1 post · 4 votes

Hi guys! My wife and I work in healthcare in the Portland, OR area... and we get absolutely obliterated on taxes :(

Anywho, for the last two years I have been reading about taxes and real estate whenever I am not in the hospital, and I have come up with our strategy. We swung and missed Q4 2025 on a STR in the Mt. Hood area that was going to do well, and I am trying to acquire two STRs this year (probably one around Mt. Hood and one at the coast). That being said, I am open to other places if I can fly there easily and the numbers make sense. By 2027, we hope to pivot to LTRs and to have my wife pull back and qualify for REPS.

Looking forward to networking, and please let me know if you know of any opportunities that might fit this plan!

- Travis

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Chris Watkins
Lender · Eugene, OR · Member since 2021 · 245 posts · 154 votes
8mo
Hi Travis, welcome to the forums!
STR's are a business and need to be approached as such. They are a lot more work than LTR's, so the tax (I assume you're referring to income taxes) savings has to be balanced against the additional time/money investment.
The income in Hood River can be good as well as the coast, just be wary of shifting regulations. The coastal towns especially are finicky on what uses they allow where. If the vibes in a town shift against STR's they can be banned and your property value goes down.
Make sure you're working with an agent who knows the STR market and can advise you well. I know a couple on the coast and in the HR market, let me know if you'd like recs.
I work with STR investors often and am happy to craft a strategy and run scenarios on properties if that would be helpful!
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Basit SiddiqiBusiness Member
Accountant · New York, NY · Member since 2015 · 8k+ posts · 3k+ votes
4mo
If you acquired a STR in 2025 and plan to acquire a couple more in 2026, I don't see a reason that you wouldn't see a decrease in your taxes.

If the average stay is 7 days or less along with your self-managing the properties, you should be able to treat the properties as active instead of passive. This means that you would be able to offset the losses against other forms of income such as wages, interest, dividends, etc.
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Ryan ThomsonBusiness Member
Real Estate Agent · Colorado Springs, CO · Member since 2018 · 1k+ posts · 1k+ votes
4mo
Depreciation is probably the biggest lever you're not using yet.
On a $300K property (land excluded, so maybe $250K depreciable basis), you get roughly $9,000/year in paper losses just from straight-line depreciation over 27.5 years. Zero cash out of pocket. That alone can wipe out most or all of your rental income for tax purposes.
If you want to offset W-2 income, there are two real paths: real estate professional status (750+ hours in real estate AND more than any other profession) or the short-term rental loophole. The STR route is more accessible for most people still working day jobs. Rent on Airbnb, materially participate in the property (roughly 100+ hours, more than any other person involved), and those losses can flow directly against your ordinary income.
Cost segregation supercharges all of this. A study on a $300K-ish property can front-load $30K-$50K in year-one deductions by reclassifying components from 27.5-year schedules down to 5 or 7. Bonus depreciation is still partially in play (60% for 2024), so that math adds up fast on your first or second deal.
One thing new investors consistently miss: you need a CPA who specializes in real estate. A general tax pro will file your return but leave a lot on the table.
What's the situation? W-2 income you're trying to shelter, or more about maximizing cash-on-cash going forward?
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Robert EllisBusiness Member
Developer · Miami, FL · Member since 2014 · 3k+ posts · 1k+ votes
4mo
Quote from @Travis Eurick:

Hi guys! My wife and I work in healthcare in the Portland, OR area... and we get absolutely obliterated on taxes :(

Anywho, for the last two years I have been reading about taxes and real estate whenever I am not in the hospital, and I have come up with our strategy. We swung and missed Q4 2025 on a STR in the Mt. Hood area that was going to do well, and I am trying to acquire two STRs this year (probably one around Mt. Hood and one at the coast). That being said, I am open to other places if I can fly there easily and the numbers make sense. By 2027, we hope to pivot to LTRs and to have my wife pull back and qualify for REPS.

Looking forward to networking, and please let me know if you know of any opportunities that might fit this plan!
- Travis

Welcome, Travis.
If I were in your position, I'd spend as much time underwriting the market and regulatory environment as I do underwriting the property itself. A lot of investors get attracted to STR revenue projections, but what matters most is whether the market can support your business model five years from now, not just today. Mt. Hood and the Oregon coast can work, but I'd want a very clear understanding of permit risk, supply growth, seasonality, and what my backup plan looks like if regulations tighten.
The reason I say that is I've seen investors buy great properties in markets that later became much harder to operate. The investors who tend to do best have multiple exit strategies. They can run the property as an STR, mid-term rental, or long-term rental if conditions change. That flexibility protects both cash flow and long-term appreciation while reducing regulatory risk.
I also think your plan to eventually transition toward long-term rentals is worth modeling now rather than later. Before buying any STR, I'd ask whether the property still makes sense if occupancy drops or if it needs to be converted to a different rental strategy.
What metrics are you using today to compare potential STR markets against each other beyond projected revenue?
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