A while back, I bought my first property - a single family home from a FSBO outside my hometown in Northern MI (a fairly happening summer vaca destination).

I am also open to Airbnb as a destination location. 

Based on your goals, I would highly recommend considering short-term rentals (STRs) as a potential investment strategy to generate monthly cash flow as a passive income.While Boston may not be the best location for STRs,there are plenty of other cities and vacation destinations that can generate way higher monthly cap rates.

Looks like you do a lot in Destin.

The location I have my eye on is a 3 hr drive from my home in a vacation destination. 

And as long as Maui remains a popular tourist destination, there will be demand. 

Brainstorming here: I had to look at a map, but I wonder if you could reach out to some Atlanta industrial brokers to see if any of their clients would need distribution in between Atlanta and some other destinations?

Saw some of the more popular markets in Ohio mentioned as a good destination.

Yes it's Hot, Yes there are areas that are not great, however the location is not only good for LTR but for short term rentals as well considering the destinations areas near by such as  Shasta Lake, Whiskey Town Lake, Mt.

I heard a lot about Gatlinburg TN, Destin FL amd my brother in law just purchased a 6br/5ba in Orlando Fl for a STR.