Mooch living with me

I have a friend that I've known for about 30 years. He's one of the few friends from that time that has stuck around through my own personal problems. He makes money by selling a particular product (not drugs) that was lucrative in the 90s but has fallen significantly since. He was a caretaker for an elderly gentleman, a WWII vet, who died last year (not from COVID). Because of the downturn in his sales I believe he was relying on the vet's SS checks to get by, but even then he was borrowing money, especially from me. He was kicked out of the trailer he had with the vet for non-payment, then moved in with another elderly gentleman who had others living there too. From what I've gathered, he started borrowing money from those others with promises of paying them back. But as with me those deadlines never materialized. Because of problems he was creating with those others, he left there and stayed with me, unannounced and uninvited for about 3 weeks. Then he went back there to find those others had pawned some of his possessions to pay themselves back what he owed. He left there again and back with me, again unannounced and uninvited. I'm single, living in a 300 sq. ft. studio apartment with one bed, still unemployed due to the pandemic, and on food stamps, plus going through some medical issues: since there's only one bed I've been sleeping in my desk chair which has exacerbated my edema (swelling of limbs), swelling my lower legs, ankles and feet to twice their size. Also, the apartment lease says only I can live here, no one else. He has SOME money that someone recently sent him, and had to pay an overdue storage unit but didn't have enough, so I lent him $600. He is about to make a sale supposedly for several thousand dollars that he says he'll pay me back with, but I'm unsure when or if it'll go through, and if he'd leave thereafter. I'm the one that mostly buys the food, and I control how much I buy because he eats 2-3 times more than I - he has no concept of conservation or money management. I have money, and I make money online on the side that helps extend what money I have, and it's likely I'll return to work very soon, but my edema would cancel that (manual labor and restricted mobility don't mix). I'm a timid, quiet and reserved person. I'm not a threatening sort, hardly ever raise my voice in anger, never use profanity around others, but it's a different story inside my head: I stew in rage and curse like a sailor. If I kick him out, he may not have anywhere else to go because it's unlikely he'd return to where those others are. If I don't kick him out then I'm in violation of my lease, and I continue to have edema for not sleeping properly making returning to work impossible. So, should I kick him out which may make him homeless, or should I let him stay and risk getting evicted, and/or continue having my health problems? Or does anyone have any other ideas?

One thing - YOU are rewarding him for this behavior and YOU are the one who has to suffer, not him. Of course, he may be a good friend, and truly care and not realize he is playing the pity card to borrow some free money he may not pay back. BUT everyone has boundaries. It sounds like you have provided help, and have even lent him your bed even though you have health problems?? In this case if I were him I would have already paid you back because I am CONSIDERATE and that's how a good friend should be, and slept on the floor myself and given you the bed because I am still a GUEST/FRIEND. He has been rewarded by others as well for mooching. He will continue to do this until boundaries are set.

One more thing - sometimes too much help may enable people to not realize their true potential. It's tough love, and lots of parents utilize this/leave their kids alone to help their kids grow up. Sorry but - a mature, responsible, considerate friend would not subject you to this kind of treatment.

First and foremost, take back your bed! He should be sleeping on the floor. Plus instead of bailing him out, show him how to make side money online like you do. I hate to say it and please do not take offense but you are not being a good friend you are being an enabler. The first go round of letting him stay was nice but the second time around was beyond nice. Set a date for him to move out and put it on paper and make him sign it. If he refuses that is enough to show if he is a true friend. Plus i think your not realizing how resourceful he is, he has gotten by this long, he can figure it out. Hope this helps,