Possible Landlord Retaliation

Here's why I'm worried now. I just thought of it today.

On March 25th, I mailed my April rent check, as usual, to the landlord. I have been doing this since I moved in and there has never been a problem with him receiving my check or cashing it. Rent is ALWAYS paid on time and in full.

On March 28th, I received a response to a question I had posed to him exactly one week earlier. I had asked him if he'd let me out of my lease just one month early. So, instead of May 31, I asked to get out April 30. He says yes, but that he's going to keep my security deposit or I will have to finish out my lease.

We decided to wait it out until the full end of the lease, although not happy about it at all because we're dying to get out of that nightmare of an apartment.

On that same day, I sent him a 60 day vacate notice, explaining why I will not be renewing my lease (because the place is a nightmare!). The lease only asked for 30 days, but I thought best to give extra notice. I sent the notice certified mail with return receipt. He received it on March 30th, officially.

Pissed off that this guy has been lying to me, walking all over me, making constant excuses about not properly doing things or fixing things, and not letting me out of the lease (when he has done this for two other tenants in the relative past), I go and read the MA tenant rights handbook and law.

On March 29th, I send him a demand letter for the immediate return of my security deposit because he never provided me with where it was deposited and what not (we have been living there for 10 months already), as required by MA state law. I sent it certified mail with return receipt. He received it March 30th, officially.

He calls me after receiving both letters on March 30th very upset and with an attitude, requesting that I provide him with proof that I even paid a security deposit. Mind you, just two days earlier he said he'd keep my deposit if I moved out thirty days early, even though he was going to legally let me out of the lease. But like I said, we decided against it, simply because it all sounded shady.

I send him photocopies of my receipts along with a follow up demand letter, marking the time and date of our conversation that took place regarding the original demand letter and his request for proof. I send that certified mail with return receipt on March 30th. He should receive it on either March 31st, or April 1st. Unless, he retaliates by refusing to sign for it. Which is not the biggest worry right now.

Okay, so you remember how I said I mailed him my rent check on the 25th? That was only sent using first class mail... no tracking or proof of delivery. And it hasn't been cashed yet.

I just started worrying about if he's going to retaliate by saying he never received the check?

What should I do?

Should I call him and ask when he plans on cashing it, even though he's furious with me right now?

Or should I wait until he says he didn't receive it, then tell him that I sent the payment as usual, on time and to the same location, and I see this is his retaliation for my demand letter? .. And that if he doesn't cash the check that I am quite sure he received, he will have to pay for cancelling the check? I will then go ahead and send another one out, certified mail with return receipt.

But see, I'm thinking he's shady enough to do something like this. And because I didn't send the rent CMRR, I have no proof that he received it, even though there was never a problem with my checks until I sent that demand letter he is now so very angry about. Can I go to court and use that as a form of retaliation if he tries to evict me for nonpayment if he won't pay to cancel the check???

This is just hypothetical. It hasn't happened. I just thought of it and am worried that it actually might come true. Also, I'm a Section 8 tenant, so if I get evicted for nonpayment, I lose my Section 8 for 10 years! I didn't think of this until now and am now regretting not sending that last check CMRR. But I didn't do the demand letter until after I sent the check anyways, so I wouldn't have thought of it to begin with.

I just need a paper trail in case this landlord wants to be a bigger bully than he already is.