I hadn’t thought about the risk of expanding my portfolio by having multiple properties over leveraged, although that seems to be a growth strategy that many use,  I’m not sure it’s one I’m comfortable with.  

However, consider STR seasonality, local regulations, and management demands, and ensure your equity loan and new primary residence costs fit comfortably within your budget.

Depending on comfort and cash, it might be a viable option as you can build equity and then sell without having capital gains, assuming it's your primary residence and you've lived there for 2 years.

Off market deals usually have nonrefundable deposits and a clunkier process that isn't as suited for out of state people until they have good contacts in the area to evaluate the property (mostly contractors that feel comfortable evaluating projects for you).

I have owned so many properties in NY that were long-term rentals and it is renter-friendly, but if you choose correctly, you won't really ever care.Meetups are a great way to add to podcasts and books.

They/you can't choose the carrier - their software assigns it.Fortegra is one of the carriers (paper in insurance parlance) that their product is written on.That said, Fortegra is A- rated I believe by AM Best so that isn't the issue.I'm going to take a guess and say that your umbrella is written with PersonalUmbrella.com (Markel) and they require all underlying insurance to be A-rated but also with an admitted carrier. 

You could choose to let your mother stay in the property rent-free.

but house hacking is the best way to get started wherever you choose.

It's very unique and I think would be attractive to guests looking for a comfortable get away in the mountains. 

This cannot get passed through until the commissioners review and choose to vote on the bill.