The nicer the area, the more rent appreciation that is predicated; etc, the lower my acceptable COC would be.I’m buying a small building in NYC, I can’t reasonably expect a 10-15% COC there.

Department of Agriculture may have information about service animals but they do not create the laws.ADA covers public spaces.Fair Housing covers residential rentals.I wrote a blog about it HERE and it should answer all your questions.The short version is that you already accept pets so the only request for accommodation would be to waive any pet fees or deposits.If you do this enough, you'll learn that the emotional support animal laws are absolutely abused.

This is changing and some landlords/property managers are accepting anywhere from 4 payments to a month-to-month with a small convenience fee added.- There is a service fee for building maintenance.

While it’s a little messed up from a social perspective, gentrification (particularly younger folks) coming in usually means an area is turning, at least for a lot of the hot areas ITP.

Social stability, economic stability, political stability, etc.

I then go on social media and try to find one of their relatives, then you can send them a personal message. 

Other than contacting former guests, posting on Craigslist and social media (which has only given me leads that don't turn into bookings), what should I do to help get these months booked up?

Because the winter market in general is slower, I'd require them to accept this Dec appraisal.   

@Courtney JohnsonA covered land deal is when you think some piece of land will have redevelopment potential in the future ie. it will sell for way more than you'll pay for it now due to appreciation, but in the short to medium term you find some use that pays the bills and generates an acceptable return. 

So if you're really good at say marketing or social media you can fill a role, if you're good at underwriting or with numbers you can fill a role.