You are on your way to having a nice portfolio :)

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

If you saying you want to do this in NY is only a result of you wanting to live in NY - then consider the option that you could purchase an out of state rental, cash flow, and use that cash flow to help payoff a nice rent in NY.

Nice lake. 

A well written management contract should clearly spell out what is expected of both the PMC and the owner, to PROTECT both and avoid misunderstandings.

The "you lucked out because of nice people" is the idea.

Hey Andrew, nice meeting you!

Now that I can see your face, you seem like a real person to me and honestly, I probably would have written something a little nicer without thinking about it.

It's your agent's job to play nice with others while also keeping your best interest top of mind.

It is a written requirement in every mortgage I've ever seen.