Should I Give Up, Or Should I Just Keep Chasing Pavements Even If They Lead Nowhere?

I am going to spend my entire life in a small claims court.

First, I have a dispute with my landlord back in Boston. I broke my lease to move out two months early. When he returned my last month's rent (there was no security deposit, and by the time I decided to break the lease, I had already paid for the last month I lived there), he deducted the broker's fee for re-renting the apartment. This resulted in my receiving back about half the amount of money I expected. I don't think the landlord is entitled to charge me the broker's fee or any portion of the broker's fee. Naturally, I can't find my lease. I remember reviewing it at my office when I initially contemplated breaking the lease, and I don't recall seeing anything about my bearing responsibility for the broker's fee if I broke the lease, but without the document in front of me, I can't be sure what it says. I do know that he failed to return to me the interest earned on the last month's rent, which he is required to pay. So, now I'm having a friend of a friend who knows landlord-tenant law assist me in drafting a demand letter for the return of this money. In the meantime, I can't cash the check for the amount he did send me (which, while not enough, is better than nothing) because to do so would indicate my acceptance that that was the amount he owed me.

Second, I now find myself at odds with the management company I used to oversee my apartment while my tenant occupied it. As part of the relationship, they retained $1000 in case of any emergency with the apartment, which makes sense. The tenant moved out at the end of last month, and they are now telling me that they will refund only $845 of the $1000. The tenant allegedly overpaid his rent by $5 one month, and they intend to charge me the $150 of management fees for the quarter beginning July 1. My contact person at the management company tells me that they normally require six months' notice for terminating the management contract. Six months. Mind you, the lease that the management company drafted requires the tenant to give only two months' notice of his intent to move out. So, basically, they have crafted these contracts so that they will more often than not receive payments for doing nothing. If they don't give me back my $1000 (or at least $995, since I understand the bit about the $5 overpayment), I'm taking them to small claims court in New Jersey for $150 plus costs.

I hate this shit. Seriously. Loathe. It may be weird for a lawyer to say this, but I detest the ugliness of lawsuits. It all seems so petty and grasping, and I hate arguing with people. At the same time, and more importantly, I need the money. I currently have no job. The total amounts at stake here add up to about $900, which is a good-size chunk of change even if I were working. Since I'm not working and I was counting on this money, its size and chunkness assume even greater prominence. At some level, I wish had the financial wherewithal to say "fuck it" and just let these thieves fleece me because it isn't worth it to quibble over the money. At another level, I think it's important to stand up for myself and demand they pay me what they owe me, even if it inconveniences me as much as it inconveniences them.

Inconvenience is really what both situations boil down to. These people held money of mine that they were supposed to return to me. They chose to withhold part of it for dubious reasons. Now, they hope that I will deem it too inconvenient to try to get the rest back and accept the amount they choose to refund. I, in turn, must endure some inconvenience and inflict some inconvenience on them as well in an effort to recoup what they stole. It is unlikely that I will be able to get back everything they owe me, but at least I hope to recover an amount that will make the inconvenience in getting it worthwhile.