@Caitlin DiBenedetto Definitely thinks you should keep the property. You own it free and clear and that is hard to come by. Plus, there are lots of options to fund the repairs. Overall, I think you are in a pretty good position.
Your tenants seem normal. They don't want rent to go up and they don't own the property, so they don't take great care of the property... Sounds normal to me.
You are a flexible landlord, meaning you will work with your tenants. That's not necessarily a bad thing. Life happens to people and sometimes we all need some slack. That compassion and understanding has value. People will want to rent from you.
However, too much compassion can obviously be problematic. That is not to say you are the problem. You are who you are. Any management structure always has two pieces. The good cop and the bad cop. The good cop builds loyalty, which you clearly have, and the bad cop lays down the law.
Since you are charging them only 50% of the going rent, it seems to me you have plenty of room to raise the rent for a property manager.I wouldn't be too worried about the tenants leaving. Even if you raised the rent to 75% of the going rate, they might complain, but they won't be able to find a better deal anywhere else. And if they leave, at 75% of the going rate, you should be able to fill the property quickly.
Anyways, with a property manager, you will have someone to lay down law without you being the bad guy. Some people like being the bad guy and others do not. The property manager can handle raising the rent, charge fines for damages and keep everyone accountable. The tenants won't like it, but that will be the point. Then you will come in, give the tenants a high five, lifts their spirits and keeps them renting for you. The good cop bad cop routine.
Once you feel like your back in the diver seat of your property, I am pretty sure you will find some solutions for the repairs.