Tough one to answer as it depends if this is a $1M property or $100k property.

Short term is always tough but not impossible at all especially with the high level of education and good hospitals in MA.

I have not explored 1031 exchange but given current interest rates may be tough to find a cash flowing deal elsewhere.

In Oceanside, New non-hosted STRs are prohibited outside of the Coastal Zone as of February 10, 2024.Most HOA's do not allow rentals less than 30 days so that is likely not an option unless you find a couple of places on the water that allow it but usually tough to find below $1M. 

Consider different strategies like mid and short term rentals as I believe the Portland area would allow for success in both (although I have heard Portland proper is tough on STRs).Best of luck!

From what I have tried to read from a non partisan site (tough to find nowadays) I believe the issue has been insurance companies lost billions in the past five years and the past 5-10 years have had the most costly fires ever.

Yes, this is "tough love", but you won't survive in this business if you let it affect you:)

It's tough, the rents have gone up so quickly over the last few years that rentometer has had a tough time keeping up. 

@Jaron Jackson, unfortunately, this one is going to be tough.

@Sanjeev Advani I’m not saying they’re all like this but since Circle K bought 3 local convenience stores they have never been able to staff them properly or maintain employees.