Hey @Ryan Cullen I am on my second house hack just north of Boston and also have my RE license.

They definitely want a small town feel, with convenient arts/culture/transportation amenities in the surrounding area.

While walking the blocks of Boston Edison, I had a chance to spend a day with a property owner as he was rehabbing himself and one thing that he did point out was in such district you have to use only zone approved paints/colors as well as windows.

Not to mention storage & transport is a lot easier. 

I am in Boston and manage properties for friends:I provide a copy of tenant ID to the landlord and ask the tenant to sign W9 so I can deposit their security deposit.

Things to consider about location: Close to public transportation.

Just like a big storm coming across your area, that is not the best time to book a flight, you are better off waiting to see if it passes and maybe take a train or alternative mode of transportation that is less risk and would get you where you want to go but maybe a little slower, but you know you get there.That is how I feel about traditional real estate right now.

Im new to Boston or just the north as a whole so connections are definitely not there.. anyone open to mentoring or guiding me to the best REIAs?

I've seen people looking for a unit in the center of Boston for that price.

I’ve house hacked twice just outside Boston and it was the best decision I ever made.