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

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

Without writing a book, google these two terms.Zombie CondoHOA Special AssessmentThen search for news on condos in Florida from this year.

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

Connect with a local architect who specializes in new construction duplexes and get their feedback on the highest and best use of the land, as is.

I am the VP of OmniKey Realty LLC and we specialize in working with investors to grow their real estate portfolio.

In terms of the upcoming zoom meetings- asking tough questions is difficult.

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.

Myself, I specialize in Section 8 and low income properties.

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!