The insurance company got bought out and the new company decided not to renew the insurance policy because of the brick foundation (earthquake hazard). 

My background: I have zero experience with real estate except for owning my own home.  

I would suggest calling more lenders and ask what their policies are.

@Dave OlversonThe open door policy is a good policy to me.

The language in the housing report was that Stows laws were prohibitive of rental housing unless it is a 40B development, so there are a couple 40B developments  that solve the affordable problem, but there is still zero rental properties for those with higher income that rent. 

Talk with your insurance agent to make sure you have the correct policy(s) in place if/when you decide to rent it out to another individual.

     It really does depend on your personal risk tolerance and financial abilities.  

Being the first one, it is likely that I'll make some mistakes that I can learn from, but they will be mistakes with only 2 or 3 zeroes after them, not 5 zeroes.Good luck!

Also if you choose the lender title service you get your title policy for free.There is only 2 options for getting the occupants to leave , (1) cash for possession (2) writ of possession  court order.

Being up front and open is the best policy.