Whenever you are buying a property out of state you should do a few things to ensure it's as smooth as possible.

My hope is that all of the personal and professional preparation will smooth the transition for my family.

I did the same and transitioned in mobile homes.

Anyone navigated a similar transition?

It is definitely a working class area although it has been transitioning as of late with the new construction near Lowe Mill, Campus 805, and the Stove House. 

I would also look at which of these has the best mass transit, easiest access, and some type of amenities.

For residential (2-4 units) and if it is a flip type deal you want to work with someone who can fund smoothly with little delays.

Now it's up to building and making it work so hopefully it all goes smooth. thanks for reaching out, looking forward to good business in the future

Perhaps I'm being unreasonable and I'm the one who's in the wrong here, I'd appreciate any feedback or similar experiences.Everyone keeps saying that the first investments usually end up being bad investments and you learn from mistakes, so I suppose this was bound to happen because a smooth sailing first buy is just too good to be true :)

Agree with Charlie on short term in Boston - new regs make that less feasible in Boston proper - but I work with folks who have robust portfolios of short term rentals in Malden and Chelsea, with the transit access of Boston but fewer limitations.