You could even consider an AirBnBRRRR strategy, which combines short-term rentals with the BRRRR method.

I’ll try to keep this as short as possible I have a pretty good tenant staying at my guest house month to month.  

For anyone interested, I executed on that plan shortly after the post as an eager and naive 25-year-old.

Short term rates were 5.5 percent, two and a half points higher than what cash typically pays.  

Short answer is I reccomend talking to an accountant that understands it.

Is it Buy and Hold or Flipping or Short Term Rentals?

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?

Don't get caught up on rate for a short term loan with interest only payments. 

Treasury notes increasing have already erased the very short-lived drop in rates and now they are even higher than before the FED cut. 

That to me is not a good investment, yet everyone is still wanting to get into short term renting?