I am the lessee of an apartment in VT. Though I live here with two house mates, my LL prefers to only deal with one person on the lease, and that is myself. My roommates pay me their share of the rent and I pay the LL the whole rent every month. So while I have signed the lease, these housemates have not signed anything.
One of my housemates and I had problems that I don't think I need to go into here. Long story short, at the beginning of march I (verbally) asked him to move out. I gave him "until may" which he unfortunately misunderstood as meaning "through may". Today he realized what I meant initially, took me to task for this, got really angry, demanded that he stay until June, and threatened to get a lawyer to stop me from "kicking him out on the street". (I don't feel like that's quite fair- I did give him two months so he would have time to look for something.) But anyway, I looked up the laws and it seems like he does have the right to stay here as long as he wants until he is given an official "notice of quit" 60 days prior.
Later, he was apologetic for getting angry and the lawyer comment. I apologized for not being perfectly clear about everything and said that June would be alright. He said he would be out by then.
My question is, should I still try to evict this guy just so he can't pull this again in June? He is going through rough times and is unstable, and I really don't want to bring a sheriff up to his bedroom door. I don't know what authority I have to evict anyone, either. Maybe that's my LL's job?
What if we both signed something saying when he would be out by? Would that carry any legal weight?
Hoping it doesn't come to that.
Thanks for any advice you can offer.

You are on the hook for the lease, but the others should be listed as residents of the unit. It sounds like you need some kind of roommate agreement, so you can have legal cover if one bails on you or has to be put out. I suggest you go to a free consultation with a real estate attorney to get their ideas also.

I'm not sure about your state, but in AZ & VA any person who resided in the leased premises, must be on the lease. If they weren't, a notice of violation was issued by mgmt which required whomever was not on the lease to either vacate immediately, submit an application to be added to the lease or if neither was done, everyone was evicted within 30 days, deposit forfeited. My best advice to you would be to, in writing, give your roommate a 30 day notice to vacate and make sure you enforce it. It doesn't hurt to get some back up from your landlord. If you have other roommates, either get them on the lease with you or have a written agreement between the two of you which states how much each is to contribute to the rent & utilities and that at any time, you can submit to him/her a 30 day notice to vacate. Your best bet, if you are going to have roommates, though, is to add them to your lease. Good Luck