Don't fall for it. Don't let him guilt you anymore. If you are legally obligated to have the police escort him out, I presume you have a court ordered eviction already? He's already taken advantage of you, and if he stays, even ONE more night, he's going to cause you even more problems. Don't put up with it. I know you don't want to, but at some point you've got to stand up for yourself. Bite the bullet and call the cops to escort him off the property, and have a locksmith standing by ready to rekey the locks. He knew this was coming, he should have made arrangements. There are homeless shelters he can sleep in if he needs a bed, but at some point you have to look out for yourself. You're not his mommy!
Are you running a business or a charity?
It's pretty much a given that even if you allow him to stay an additional night that he will not vacate tomorrow either.
People who have the backbone to make a hard but smart business decision are called landlord.
Those who don't have the backbone are called suckers?
What do you want to be?
If you have a court ordered eviction with the right to have the sheriff or marshal escort him out, then you do it.
The *only* way the police will touch this is with a court order. Even if your lease says you can do it, the police won't deal with a civil matter without a judge's order to do so.
Being a landlord is a business. Don't let it become a charity.
You got a court ordered eviction and the deadline is today? DO NOT let him stay. He has had ample time.
If you let him stay tonight, what is going to happen tomorrow? Is he suddenly going to have a place to go and money to pay for it? Nope..... tomorrow will be just the same and he will be begging for one more night. Besides if your contract is from a legal eviction and you allow him to stay beyond the eviction day you may void your entire eviction and have to start all over again. Out he goes.
NO, Your property and business has been damaged. Get him out now
Okay so we have had some previous issues with our renter, he has been known to not keep his promises and likes to guilt us a lot and make excuses for things. We have been lenient to him but we are at a limit now. So the problem now is he is supposed to be moving out today before 9pm according to the contract. Legally we are obligated to have a cop escort him out of he refuses after 9pm.
However he is very financially...lacking a lot. We didn't realize how bad he was able to afford rent until later because he lead on how he could pay with no problems but that was BS. He texted me asking if he can stay another month and "promised" to pay on Saturday. However rent would have been due TODAY if he wanted to stay, so yeah he's in a tight spot. We said no but he is asking to stay one more night at least, but according to the contract he can't do that without paying for the rent for the next month.
But he literally might have 0 places to go tonight, but should I just not allow it anyway? I honestly can't stand him anymore and am happy for him to be leaving but on a certain level I feel guilty.
We do have showings like in the morning tomorrow so he might cause some issues if he stays.