What  are the implications to me legally if I rent out to a person that has filed bankruptcy? 

We will be hearing from you again on issue after issue.

Again, that's all fine and good but the numbers have to work which is why I was hoping to speak to someone with first hand knowledge of owning a property or properties in the town without an axe to grind like the Seabrook sales people.On the issue of negative STR regulations roughly half the houses in the town are in their rental program currently so I don't see that as an issue in the future as an investor as it's baked into the town's business model and not likely to change.

Conduct a thorough inspection to assess the true condition of the property.High Vacancy Rates: Excessive vacancies can signal underlying issues such as poor management, undesirable location, or an oversaturated market.

If not, I have no issues taking on a "cash paying" tenant.In terms of what I would do in your shoes with $100k... it sounds like your plan is pretty solid.

Make sure that the plumbing issue is taken care of and the attic issue has been secured and is not still compromised.

So, Escrow companies are the intermediary that handles things so the "closing" happens swiftly and legally.

I know that the rent is guaranteed, but that isn’t enough for me probably since I haven’t had very many issues with nonpayment of rent. 

If the PM is not communicating with the tenant, that is another issue. 

Hi Mitchell,From our experience we haven't had any issues renting out properties to different residents that have a single family home and a garage unit conversion on the property.