I’d like my first move to be a house hack, that would later become a straight up rental property.

I didn't quit my job straight away, mainly because i couldn't afford to, so I started RE and bit by bit closed deals until I'd saved up a years salary and then jumped in full-time. 

Seems like only one option to me. straight up, he didn't pay rent; evict immediately.

@Cory Gardner Unless it would be a solid investment as a straight, long term rental, your client should be very careful.

Yeah don't deal with agents, go straight to the buyer. 

its probably not much but if it is.. you want to know first hand. if this is your first deal.. its worth the few hundred bucks in my mind.Just think of all the Morris invest clients that if they would have just spent a few hundred bucks to go look at their project they would not be in such dire straights.. but if the TK operator is top notch like a few are there.. you can probably take their word for it.but again if your worried just run out there for a day.

Never purchased a home but I would like to go straight into multi family and live in one of the units if possible.

In my opinion, there is no straight answer.

Boston is Suffolk County, which is all the OP was asking about and the data I presented.And for the record, the data I referenced comes straight from the MLS.  

I feel like this is an easy question, just looking for an easy straight forward question.