Alot of first time cost seg folks come to us with losses generated all excited to offset w2 income, only to find out they did not qualify for the STR loophole properly and cannot use the losses against active income.

Hey Vikrant, Your STR wouldnt count for the STR loophole since its your primary residence, but the good news is the book keeping and tax situation would not be super complicated.

I would like to add what qualifies you are a short term rental investor that can take advantage of this "loophole" below: The short-term rental (STR) tax loophole allows property owners to classify rental income as non-passive, enabling them to take advantage of certain tax benefits even if they don't qualify for Real Estate Professional Status (REPS).

@Patrick Shep the STR Loophole is a great strategy. 

The law was written specifically to close this otherwise obvious loophole. 

For example, if you use the STR Loophole strategy, then you could potentially use depreciation to offset your physician income which would lower your taxable income and lower the amount paid to PSLF. 

You can usually use bonus depreciation against the asset assuming it will follow the short term rental loophole rules of 7 days or less average stays. 

One downside I see to this strategy from a tax perspective: You are unable to take advantage of the STR loophole which is a massive offset of your tax liability for many folks.

Houses in my area that don't allow pets seem to stay on the market longer and with the ESA loophole I feel like leaving the door open makes them less likely to cheat the system and just get them in for free. 

The "I'm selling the contracts, not the property" has been used for years as a possible loophole.