How to Deal With High Rent Raising

[David Santore]

New landlord here, just bought a two family and will be house hacking by living in the 2BR unit and renting the 3BR unit.  The house is coming with a tenant already in the 3BR unit who's been there for about 5 years, and has been paying a rent that is far, far below current market value (about $1,000 to $1,100 under).  The owners cut him a heavy deal because they're off site and he'd do maintenance around the house, and the owners had the house for a long time with it being paid off.

I do not want to charge such a low rent, but I also know that anyone who's told, "Hey pay me $1K more per month" will leave.  I actually only want to charge $550 more, but that is still going to be a tough pill to swallow.  My biggest concern is this guy will just squat and I'll have to evict him, which in MA I know is the worst state for this.  I'm not sure what to do in this situation?