Any good HML will be happy to share the contact info of borrowers so you can see how easy the process was and how well they treated the investor.Can you share a recent closing document or HUD?

And is it pretty easy to manage or no?

Get something durable in a color that does not stain easy and a material that can be scotchguarded and you will be good for several years.

Is RentRedi as easy to use as Avail for posting the listing and managing the listing?

You may want to find a good agent in the southern NH area as I'm hearing that market is prime for investment with people moving up from MA, but your other markets might be just as solid.Also, since you're already an agent, it's pretty easy to get your reciprocal license for NH or RI.

It wasn’t an easy path—in 2014, I even filed for bankruptcy while trying to launch a business.

In short, securing an STR permit isn’t easy unless you fulfill all the township’s requirements

The easy answer would be small multifamily or single for a long term rental. 

It's not easy to admit mistakes.I think you should start by eliminating the get-rich-quick mindset.

If you are worried about it, buy an umbrella insurance policy for $1 million and sleep easy.