Thimble does not insure short term rentals.  

Hi @Frank Pyle,**I am not affiliated with any of the companies mentioned**To secure long-term financing for your Airbnb, look for DSCR lenders that accept pro forma income instead of requiring 12 months of rental history.

I don't use padsplit (weekly rentals); I rent on long-term leases in B Class neighborhoods.

Since my first property is long-distance, I figured it’d make sense to look for my next one closer to home.

I also allowed the fear of others to take me away from my long term goals.

As long as you are following the law and the lease, you shouldn't worry about lawsuits.

Sign an Assignment of Contract:      Check the terms of the contract.      

If you plan to live there in the winters, you might have a hard time doing long term rental outside of that and finding a new tenant every summer.

In your experience, does one approach lead to better appraisals, loan terms, or overall outcomes?

They bring higher tenant turnover, limited cash flow, and attract traditional tenants who aren’t your ideal long-term buyers.