I've known a lot of landlords who got put through hell by tenants that turned into squatters. And these were in states where the rule of law was enforced, something we don't have here.
The moral of each story they told played out the same: They wished they had bribed them sooner.
If I were in your shoes, which would be gross because my feet aren't just ugly they also sweat a lot, I would be frank and firm. Tell him that you have plans for the property that don't include him being there (you can invent whatever story you want if you think it will help) and you need him, and all his shit, out by whatever date, and ask him what kind of help he needs to make that happen because the date is firm. I wouldn't offer any money at the beginning because once people see dollar signs it's easy for them to imagine them growing and they will want more later.
After that, make regular visits to check on his progress and work on the place. You mentioned drugs and alcohol, so it might give you an advantage to run things like weed whackers earlier in the morning when he's normally sleeping it off or nursing a hangover. It will feel less like home to him. You can also get a progress report and assess your future actions. Meanwhile you're getting the property back in shape.
As Eviction Day nears you'll have a better idea to determine if he's really going to leave or not. If he mentions that money is the issue, offer him some empathy and suggest that money is tight everywhere and that's one of the reasons you need him gone and reference whatever story you told during the first visit if applicable. But if it seems appropriate, you can offer him a "loan" to GTFO. Of course you'll never see the money again, but he'll be less likely to be greedy and ask for more if he believes you don't have more to give him. And whatever you do, don't actually give him the money until he's out. Otherwise he'll blow it on drugs, he'll still be there, and you'll have a worse problem than you have today.
The moral of each story they told played out the same: They wished they had bribed them sooner.
If I were in your shoes, which would be gross because my feet aren't just ugly they also sweat a lot, I would be frank and firm. Tell him that you have plans for the property that don't include him being there (you can invent whatever story you want if you think it will help) and you need him, and all his shit, out by whatever date, and ask him what kind of help he needs to make that happen because the date is firm. I wouldn't offer any money at the beginning because once people see dollar signs it's easy for them to imagine them growing and they will want more later.
After that, make regular visits to check on his progress and work on the place. You mentioned drugs and alcohol, so it might give you an advantage to run things like weed whackers earlier in the morning when he's normally sleeping it off or nursing a hangover. It will feel less like home to him. You can also get a progress report and assess your future actions. Meanwhile you're getting the property back in shape.
As Eviction Day nears you'll have a better idea to determine if he's really going to leave or not. If he mentions that money is the issue, offer him some empathy and suggest that money is tight everywhere and that's one of the reasons you need him gone and reference whatever story you told during the first visit if applicable. But if it seems appropriate, you can offer him a "loan" to GTFO. Of course you'll never see the money again, but he'll be less likely to be greedy and ask for more if he believes you don't have more to give him. And whatever you do, don't actually give him the money until he's out. Otherwise he'll blow it on drugs, he'll still be there, and you'll have a worse problem than you have today.