When Your Stomach Drops to Your Shoes

The Tenant called. I waited for F to start swearing. It rarely feels that any time Tenant calls, it is something good. This time was no different, however, F didn't swear.
 The night before a lovely high heat, high humidity day, the A/C goes out.
The hard ass in me comes out, "You know, we DON'T HAVE to provide him with a/c."
F just stares at me, then walks away.
OK, so yes, maybe we DO have to provide him with a/c, even though that's no where stated in the contract. My point is, I hate being a landlord. It seems that every time F and I plan something that requires us to spend money, something at the Rental goes awry. This time? Replacing the ceiling in the 3rd bedroom that is frontin' as our dining room. That in itself is a story. 4 coats of paint bubbled and peeled off like pulling a sticky note off your desk. All my hard work, undone. Everyone we spoke to was baffled. Except Eldest Sister. "Sounds like moisture to me, a ventilation issue." Ah, her environmental engineering degree finally comes in handy. All 3 of the contractors we had come in to look said the same thing. So there goes $850. Plus whatever is wrong with the A/C that we are having professionals look at.(Tenant still has not called them, so he is still without a/c. His own doing.) Not the guy F knows who took 5 days to fix our A/C in 90+ degree weather. Yet another story.  Anyway, every time Tenant calls I dread what I'm about to hear. My stomach drops to my shoes. I love my old house, I really do, but like many people in the good ole' USA, I'm "under water" on it. And there is no way Tenant, who filed for bankruptcy in the past, is going to be able to get a loan for any amount that would come close to paying it off.  *sigh*
I guess the good thing is he wants to sign on for another year, however, with the clause that if he buys a house he can break the lease without penalty. My thought on this is, what if he just wants to break the lease and is just SAYING he's buying a house? Can I force him to prove that he's buying a house in order to break the lease? I just don't know these things. I am a lazy landlord. I am a lazy landlord because I don't want to BE a landlord.  I hate the feeling I get when Tenant calls. The overwhelming dread. The worry about how we are going to cover whatever expense is going to come up this time. The tense between F and I over it. We need to sell it, and be done with it, but in today's market? Um, yeah.

Any suggestions?