There were some external problems that caused 2ft of drywall from the floor of the basement to develop humidity and needs to be replaced.

A great idea here would be to create the site yourself externally and simply use the Hospitable widgets integrated on your website to get all of our PMS functionality on the website that you own.

With a $60/mo HOA(external maintenance not included with the exception of fencing) and 6.5% interest rate, my monthly mortgage (with taxes, insurance, HOA, etc)  will be around 2600/mo.

We have lived there 5.5 years now with one tenant who I brought with me from the previous property and was hand picked.

They don't like external links here, but you can find it easy enough: Tampa Bay Real Estate Investors with Jeff Copeland.

They were pretty much recommended and handpicked by a contractor I had hired for reno.

There are often things that can be done externally to help with the situation.

Why hire a CPA then question them externally?

RE, specifically, will be a lot more volatile and have so many external factors knocking at you that you will have to be resilient.

So I have some knowledge about what you are contemplating... but even with 37 doors,  I wouldn't even start to think about 1,000 units or something crazy like that without significant external resources and partners, and even then you are probably talking about a syndication deal with lots of investors.