It's unprofessional and potentially dangerous.....Write him a check.

I agree with what you’re saying though, it could be dangerous for a newbie like myself to jump in face first when I don’t know what I don’t know

Once they realize what a great mitigator of inflation it is. 

I have researched all over and thinking of a couple of moves and would like some expert opinions:1) What do you think of Roofstock- my only fear is hidden costs, or tenant turning into squatters, or no tenants after a few months- how to mitigate these issues.

I know about the dangers of the due on sale clause but it seems to me that a lender who has a mortgage from any time in the past is likely to have a higher interest rate and therefore would be less likely to call the loan due in the current environment with the low interest rates. 

I'd be curious to know what other proactive measures people are taking with properties in at-risk areas.Also, I have 2 insurance policies, one is your standard property insurance, and the other is a liability-only insurance designed for short-term vacation rentals.I'm curious what products or services insurance companies might offer that can support risk-mitigation.

To me risk mitigation is a process that comes through responsible property selection, tenant selection and day to day responsible operational management activities that are hard earned over time, rather than Rube goldberg like gimmicks/tricks cavalierly layered on top of generally passive activities regardless of appropriate fit or not.LLCs certainly have a place for certain active businesses of scale that face certain real liability risks.

According to the sub contractor, they did the work before approval because they thought it was a danger to my property which I appreciate but also feel it couldn’t have been that hard to get a hold of me, or the PM to get ahold of me to approve a work order of that magnitude.

However, I highly doubt this neighbor presents any danger to the community at large.

You are too dangerous and will loose your own money.