(adjust cost basis - net sale = net gain)Once you have that you can deduct state and federal taxes from that figure.It doesn't sound like it in this scenario, but if you have lived in the property for two out of the previous five years you could qualify for the 121 exclusion.

They either do or don't qualify.

The listing is currently visible as ready to be in service, and I've already received three bookings.My question is, will I still qualify for the short-term rental tax benefits or loopholes if I have blocked off dates until September 19th due to these repairs?

Not true, but don't believe me or anyone else, go find the answer from qualified tax professionals!

So you qualify for both $500K tax free. 

This way, both of you would own the properties together in the same entity, making it easier to qualify for a 1031 exchange when selling and reinvesting.2.

I recently learned that if you owner occupy a residence for part of the 5 previous years before sale, and you rent it for the remaining time, you can calculate the percentage of time the property was owner-occupied (and thus qualifies for the sec. 121 primary sales tax exemption of up to $250k for single filers) vs the time it was being rented (which qualifies for 1031 exchange) and claim both benefits. https://hcsequity.com/blog/combining-1031-exchange-with-121-....How does this work for a multi-family?

Find out how much you can qualify for and if it's enough.

Hindsight is 20/20 of course but this is advise borrowers to go the conventional route (assuming they can qualify of course) because it is a cheaper loan then FHA with the MIP for life. https://www.bankrate.com/mortgages/remove-fha-mortgage-insur... 

A qualified professional appraiser will generate a comprehensive analysis considering factors such as sales comparisons, highest and best use, market conditions, and income generated following Uniform Standards of Professional Appraisal Practice guidelines.