It has not been well maintained over the last 19 years with a string of just bad renters and the person I had managing it just didn't do good quality repairs or work to it. 

Ideally, I would STR it to either the wedding hall or seasonally, although the purpose of snow-birding is to be in CT in the summers (wedding season) and Florida for the winters.

Everyone is going to give you their own "personal" preference.

It only says "some personal use" with no quantity specified. 

They will allow your mortgage payment and any personal debt payments (credit cards, cars, etc) to reach about 45% of your monthly income.Programs vary all over the place so it's best to ask a mortgage broker which programs you qualify for.They like two years on the job, rent paid on time, no liens or judgments, pay stubs, tax returns and so on.FHA has a 3.5% down program plus closing costs.

I personally use US Bank [Big stable bank with Zelle capabilities], Relay [Checking and Savings 3%] and then Quickbooks [high interest rate 5%].

But I get it if you can invest 500.00 U certainly cant buy whole notes or secured positions with such a small amount. becomes a personal decisions make 7.5% with risk of losing it all or buy T bills for about 5% with zero risk.. its up to the individual investors.

My next step after posting this is to reach out to a few similar hosts for the style of property I am looking to invest in and see how well they do on a personal level.

Find a group or person that can give you both education and mentoring. 

It also takes a personal guarantee from the borrower.