WIBTA If I took my tenant to small claims after evicting her?

My tenants are my friend Z, and his GF, Carole Baskin. Their lease was up at the end of May 2020. In Feb they told me they were moving to Michigan to be closer to Z's family and wouldn't be renewing their lease. I said that I would be putting the house on the market closer to the end of their lease as Carole has 3 kids and I didn't want them to feel like they were being pressured to leave.

In March, Z asked if they could stay through the end of Nov because he'd lost his job and they were struggling to get the money together to move. Carole cannot hold a job, and the few she had have been under the table cleaning gigs. I said yes. A few months later he asked if they could be out by the end of Sept instead, to which I said yes.

Mid July I brought my realtor out to view the house. It was trashed. Bags of garbage everywhere. A 2 car garage so packed with junk that neither car fit. They got ducks and let them shit all over the covered porch in the back. The glass walls in the guest shower had been broken out and replaced with plastic and blue painter's tape. Carole low-key accused me of infesting the home with fleas (they had 3 dogs and 2 cats at the time). I set up a date to come photograph the house for the listing 5 weeks later (mid Aug). I reminded them a week before and confirmed with them again 3 days in advance. When my spouse and I arrived to photograph the house, there was garbage piled up on the front porc, a dumpster out front, and the house was still thrashed inside. We couldn't use any photos and had to use photos I took during the inspection. Turns out the fleas came from a couch they bought. The infestation was so bad they ripped up the carpet in the house. The carpeting on the stairs to the basement was pulled up because their animals shit and pissed on it so much they couldn't get the smell out.

Didn't list the house until late Sept and found out they were breaking up. Z was moving mid Oct, Carole said she would be out by the 31st. I only found this out because Carole signed up for rent assistance and the organization told me. I offered Carole several options - paying for moving/cleaning help, a 6 month lease, or $500 cash if she moved out by the 15th (rent is $600). She declined all of it and saiid, "You can't evict me because of COVID.” So, I got a lawyer and served her. She was supposed to be out by NYE. She waited until 1.5 weeks before she had to be out before getting a pro-bono lawyer to contact mine and request she stay through June 2021. Mediation ensued. Bc I didn't get the second lease in writing, I screwed myself over and she is now in my house until the end of March.

These past 2 months my realtor has been encouraging me to take her to small claims court after she is out. Based on how things looked the last time I was in the house, she's probably caused a couple thousand in damages. WIBTA if I took her to small claims court, knowing I won't get anything and knowing it will likely affect her ability to rent in the future?