I get this letter saying really a bunch of nothing, asserting that I willfully with held the security so now I owe them double security and if I don't pay them by X date they are authorized to file suit in Vermont SUPERIOR court.So, can they actually take this to the superior court as even if they were to tack on lawyers fees I can't imagine it would make it past 5k?

Sharp doesn't mean an Armani suit. 

If the attorney says this is more suited to a limited power of attorney, then go for it. 

We ended up buying a house in Southside district (great for gameday), and may end up fixing up the master suite with separate entrance for AirBnB on special weekends.

It didn't mention any backing/guarantee, insurance requirements, or even background checks.You would need to go after the contractor and hope that he was sloppy in his entity creation or that the "other side of his business" still has assets and was part of the same entity.You also may be able to go back to the insurance company to see if they will help with the filing of the suit.

Some of my recommendations are:- Be a professional (That does not mean suit and tie or anything outward).

Sure there is a relation, but there are a number of other ways you could generate cash that may not involve real estate at all, but may be more suited for you. 

This would be better suited for the single-family forum.

Work on yourself, learn to love the process, and the results will follow suit.

Here are some things to think about and consider:We only do AirBnB, and use Instagram and Facebook to help market it.