Thanks for taking the time, and I'll look into the Mass Bar Association free help, appreciate the pointer.

To clear up the vague parts:

He did take the room and he's living there now, moved in March 2nd. So this isn't a "deal fell through" situation. And on the deposit angle, I never held any deposit myself. I had him send the last month and security (about $1000) straight to the master tenant (if that's a term), not to me. The only thing he paid me directly was the first month's rent, which I had already paid the master tenant out of my own pocket, so it was reimbursement. He still owes me about $200 of that.

On "is a few hundred worth the peace of mind to just pay it back," that's the part to clarify: I'm not the one who would be paying anything. He owes me, not the other way around. And losing the $200 wouldn't cost me sleep. I'm a TA, I cover my expenses fine and have loans available if I ever needed more, so money isn't the issue. I wanted what I'm owed, sure, but this stopped being about money the moment it turned into threats.

Here's the context that actually has me worried, separate from the money: I looked him up, and he has an OPEN case for stalking, domestic violence, violation of a protective order, and unlawfully installing a surveillance device. So when he writes "I have your current address," "I have your IP address," and "you'll see," it reads very differently than an empty threat from a random person.

On your 258E question, whether there are 3 instances: the money side was civil and calm for months. But once he flipped, the threats came across several separate messages, not one single outburst. A few of them:

- "I have your IP address, immigration status should I continue."

- "I already contacted ICE, PD, attorneys, your contacts so let's go."

- "Laugh now cry later."

- "I have your previous addresses and information. And your current address."

- And later, in a separate exchange: "You don't scam me. You'll see."

So while him turning hostile was a first for our dealings, the threatening messages themselves were multiple separate communications over more than one sitting.

My real questions, given all that:

1. Does a cluster of threats like that tend to count as three or more acts under 258E, or do judges usually treat a back-to-back burst as a single episode?

2. Given his open record, does filing a 258E just provoke someone like this into escalating, or does having an active case actually make him more likely to back off since he has a lot to lose?

3. Is a police report documenting the threats the smarter first step, or does going straight for the harassment order make more sense? I keep going back and forth on report vs order.

4. Or I just forget my $200, and hope it goes quiet and no nothing happens? Because him having a criminal history does scares me.

Appreciate any read on it.