I rented a 2000sqft home for three years

It taught me a lot about what happens with that type of arrangement. You can get tenants that are worth gold, and you can get tenants where you can’t get the sheriff there fast enough to throw their butts out. I went through both.

Two ideas for you:
1. Hire a property manager. I was managing my rental from out of state, and it was a PITA. I hired a property manager to take care of the ins and outs of the property maintenance and tenant negotiations. I found that working with a reputable property management company took a lot of the hassle out of the arrangements. They don’t have any emotional attachment to the house (not that you do per se, but you do have some mixed feelings about that house which they won’t have). It’s just a business proposition for them, and they’ll manage it as such. They’re practiced at balancing the cost of keeping a place going and finding good tenants, while returning a profit. There’s a lot that goes into property management and sometimes hiring a manager is a very nice way to go. They’ll take a percentage of the rent as their fee, but you sleep better at night knowing that if something goes wrong, it won’t be your phone that rings at 2am.

2. If the tenant really wants to get out of the lease and you want him to go, and don’t want to carry the house utilities through winter, make it a caveat that a replacement tenant must be found, which meets YOUR criteria for rental history, etc, before he can break his lease. If you hired a property manager prior to letting this guy go, they’d handle all that for you.

I got out of my rental house management after three years because it was just too much to keep up with. I had other career plans and property management wasn’t amongst them. But my dad has been a property manager now for almost 30 years, and he loves it. He treats it like a business and isn’t shy about telling tenants to shape up or get out. He’s done pretty well with that business too, better than some of his other small biz ideas. So it really can go in a variety of different directions, depending a lot on what you want to do with it.

I would suggest since your frustration level is so very high, you may not be in a position to make any big decisions right now. If nothing else, perhaps sit down with a property management consultant or mentor to help you pencil out the various alternatives and discuss which of them are really the most in step with your own personal goals for that house (and the rest of your current/future plans).