He's someone I already knew, and he does the work for a small rent discount but he's about to move out and I don't think it'll be so easy to find another qualified tenant without losing a month's rent while looking.Before I bought the building, the tenants were all responsible for taking their own cans to the road and they were collectively responsible for keeping the area clean, but they didn't (and I didn't know they didn't.) 

They either do or don't qualify.

It will not be a formal contract or agreement but something where both parties understand the objective. 

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.

(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.

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

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?

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

So you qualify for both $500K tax free. 

Tresa Todd Lutgen might be a good Christian coach convincing people to join a religion, but that doesn't qualify her as a real estate expert.If you're sincerely contemplating investing or working with distressed properties, my advice is: EITHER begin at the grassroots and start by immersing yourself in real estate as a realtor.