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Yes, too bad you didn't agree on rent in the first place so you could be even by now.
I'd give him what you can - maybe he can get an apartment with it, and agree to pay the whole amount or another large portion by a certain date. Get that loan out of the picture.
I have to think....you agreed that you would pay him back, but now that he has been free-loading off of you, (for the past two months) and his sister, plus being very disrespectful, to her, threatening to tear personal items to shreds, no....The "Free ride would end."
Seriously, if you own the place, just change the locks.
Yes, he could be a pain and claim that he lives there and force you to legally evict him, but you never invited him to live with you. If he's a stoner, he's probably too hazy to figure out how to do deal with the courts, anyway. Besides, if he gives you problems, tell him if he ever wants to see his $1,000, he can just shut up and deal with it. Unless you signed something saying you'd pay him back, it's his word against yours.
It kind of reminded me of my mother handling various and sundry family disputes, actually. Gawd I miss that woman.
Aight, so OP, pay the dang loan back and kick the bum out.
Hahaha I loved that show! Watched it for laughs. Made me feel smart.
OP needs to go to court. Make the bum leave. Calculate the expenses . Say buddy you owe us now!
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Gawd I miss that woman. 
