Going to give the owner a call as soon as possible!

I'll try to simplify it as much as possible. - CMHA shows a FMR of $1329 https://www.cmha.net/housing/landlords/rent.php (hopefully you can understand that).

But I'm pretty sure I can't find any houses for 20k around here If you want low income rentals stay as far away from NYC as possible.

I would suggest both....keep learning and start attending as many local meetups as possible. 

Ideally I can find a debt partner who's willing to gap lend those funds for a flat rate return, since the deals cash flow very well, and I'd prefer to retain as much equity as possible.

My whole thing in real estate has been to be in cash as soon as possible,  but would like to hear the arguments from people who are happy to cash flow on a 30 year. 

Then, work with an attorney to put everything in writing, covering multiple "what if" scenarios and all possible contingencies. 

So I’m considering blocking Saturday check-in/check-outs entirely. 

I plan on rehabbing the entire property to BRRRR or flip it.

If you are a landlord and not using a licensed Real Estate Agent as a property manager you can get away with not complying with all the fair housing laws, but when you are like my company and you have multiple properties available to rent at one time, that is when it is very easy to find out if we treat all applications the same across the entire portfolio.