3️⃣ Local Regulations: Before you invest in a short-term rental, it's essential to understand the local rules and licensing requirements.

The area has certain advantages like shelter from regulation risk (pretty much as low as anywhere in the country if you buy in the approved STR tourist zones) and long term security (people aren't going to stop going to Orlando anytime soon). 

We re-piped the plumbing with Pex, installed new toilets, new showers, new hoses & fixtures.

You have 22 properties that are probably at least 60 years old. 15% maintenance of $1000 rent does not get you very far when you start looking at big-ticket items like roofs, windows, plumbing, HVAC, driveway, tree-removal etc.I am doing this long enough here in Milwaukee that I own some properties I have rehabed twice.

In some cases that's amazing -- one part of the town gov't considers it to be a commercial lodging establishment so it's exempt from STR permitting and regulation. 

These programs offer options for less money down and in some cases DPA - Down payment assistance.As a banker for over 18+ years I am very skeptical when I hear a new name in the business only because its become tougher to lend with all of the new laws and credit/insurance requirements and regulations.  

No, it is inside of an HOA neighborhood but the current regulations only restrict rentals under 30 days stays.

TD and Congress needs to come up with more relaxed tax regulations to make investing in real estate lucrative again.

Start by researching local regulations and working with an agent experienced in vacation rentals.

I am not familiar with NY regulations, but investigate whether you can charge each tenant ~$80/mo for the gas (do the math).