Small claims, and what others in favor have said since JanM’s comment. In most cases, small claims is easy-peasey. There is no enforcement, as others have pointed out, but in my case, just the paperwork getting mailed to a guy who owed me money was enough to make him pay. When I first filed, the clerks recommended I cite ALL my costs including the process server’s fee, as I was entitled to all of it.
It sounds like you have a great paper trail, and she’s a punk. Teach her a new lesson.
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She’s been “living with herself” for years. She doesn’t care.
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Be careful about making that kind of assumption. You thought she was struggling pre-covid. Turns out she was making 6 figures. Unless you live in San Francisco or NYC or similar, struggling to live on $150k is more likely to be a case of poor budget prioritization anything else.
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I guess my only question is “why do you want to teach her that lesson?”. Do you think that will be an effective use of your time? Do you think she’ll actually learn it?
While I’m even personally incredibly aggravated by her insistence that she doesn’t owe late fees, it doesn’t sound like she is the type of person that will learn.
My point is not about kindness or forgiveness for her sake, but for yours. If you feel that you can execute the plan to take her to small claims without taking an emotional, physical, or financial toll on yourself, knock yourself out. But if there’s any part of you that is going to stress over this, it’s honestly not worth it. There’s a bigger emotional toll that ‘revenge’ can take, but you don’t sound vengeful so I’m not really addressing that.
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Sent the certified letter today. She may ignore it like she has my other communication, but if she does, that will only support my case more. I gave her two options in the letter. Pay $150 by 6 pm July 15 or I take her to collections for the full amount, plus any costs on my behalf in the process of collections and late fees will continue to accrue. I remind her of the language in the contract that says I am entitled to recoup all costs of collection. We will see if I hear from her.
All communication is documented in writing. And I’m documenting dates and times when I’ve tried to communicate with her and she’s refused to respond.
If this does go to court, I’m not going to mention she might be struggling now. I will mention her prior income which she’s mentioned in writing. “When I lost my $150,000 year job…”
To those of you who think she will learn her lesson, no I don’t think so. A little research has shown she’s used to losing in court.
I have no problem sitting on a judgment until she needs a new car. 
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You are very determined!
If she has other unpaid judgments, I wonder if she might declare bankruptcy?
Keep us posted on how it goes.
oh, hell to the no! I can’t even imagine the time you used to type out that entire epiphany…much less the time to go after a couple hundred bucks owed at this point. As far as ‘teaching her a lesson’. 
I"m sorry but that ship sailed a long time ago…once upon a time you may have been able to influence her (especially when her horse was alive) but much too late now. You’ve been a victim long enough. she doesn’t rate a moment more of your concern, time or effort. She’s winning .
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Agreed. Anger is hard to carry around. It has a cost, whether you realize it or not. No way would I carry around that kind of anger for $200 bucks.
My neighbor has thousands and thousands of dollars of judgements against her. She could either file for bankruptcy or just live in an ever decreasing standard of living, which is what she chooses. She cannot ever sell her farm, and will die poor someday. I’m pretty sure none of the people who filed against her taught her anything.
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In most states taking claims to small claims court, requires little time and stress.
The attitude of the former boarder just begs for a trip to court.
The experience will be good for th OP.
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I’d be so pissed but I’d let it go. Karma will get her if it hasn’t already.
No freaking way would I continue to pursue this.
Remember, money isn’t the only “cost.” Right now, you’re paying a LOT in stress, anger, frustration, annoyance, time, and general brain drain. And you have been for years. Let it go. Good riddance to this piece of work.
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