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 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?

In turn one tenant that wanted to part from the group found an attorney to dig through the lease and find a loop hole which is frightening to me. 

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

For the purpose of using the STR loophole - no.

My goal, is tax saving with the STR loophole, but also some rental income.

My understanding is you do not need to pass the “real estate professional test” for this.This seems like a big loophole for STR investors.

My question is if I'm not a real estate professional, but own an STR that fits inside the STR loophole. 

Don't think you would be covered properly with out an attorney too many loop holes.

I like to think that where there is a blind spot- a loophole is waiting to be found.