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A brief update to the roommate situation:
I have decided that I will kick him out, but this will need to be delayed for a few (as in three) weeks while I conclude the lease on the old place he was living at: get the last of the stuff out, keys turned in, power turned off, etc. If I were to give him notice now there's a chance that he would try to move back in there and squat after the lease ends, in which case I could be held liable for having had an additional tenant living there off the lease, and I don't want to get sued. I don't think that he would do that, but I am afraid that he would and I'm not sure if that's reflective of the level of scumbag I've tolerated over the last few years or the level of paranoia/dread with which I approach interpersonal conflict. I am less afraid that he will pitch a fit and punch a bunch of holes in my walls or whatever, if only because he'll run out of breath in 30 seconds. I consider it likely that he will threaten to commit suicide but unlikely that he will attempt it in a violent enough fashion to succeed. He can say whatever he wants to his friends about what an asshole I am, but it doesn't matter because most of them are ~15 years older than I am and the ones that know both of us will understand why I am doing this.
It is my understanding that per my state's laws his living with me sans paperwork is considered an informal month to month lease that can be terminated without cause with 30 days written notice (which can be hand delivered by myself, no need to have it served). If he fails to vacate by then I can then sue to have him evicted. If worst comes to worst I will ask my landlord to have him evicted at whatever price that may cost (Conveniently, my landlord is an old lady who likes me, and she knows about this roommate, so I don't think she'll elect to evict both of us.). My worst case scenario resort is to exercise the fact that my lease is month to month at this point, so I could just move and leave him there to be evicted. I don't want to do that because I'm paying below market for a nice apartment in a great location but I'll do it if I have to.
Good luck.
How are you holding up morally/emotionally? Are you alright with kicking out your friend (or "friend", depending on how you see that by now and what friendship means to you)?
It's been rough (especially anxiety-wise, but this isn't my first rodeo there and I'm reasonably competent at dealing with it at this point in life) but I'm hanging in there and am calmer about the situation than last week. My job situation is not what I want it to be but is not an outright emergency (I can string together enough delivery and bartending shifts on top of it to keep the bills paid.) so I can backburn that problem while I get the roommate situation dealt with and have a backup plan there that'll open up in a few months.
I am dreading the process of kicking the roommate out (He may legitimately have nowhere to go due to having burned every bridge, and if that's the case or close to it I expect much wailing and gnashing of teeth.), but he has more than overstayed his welcome and done less than nothing with the frankly embarrassing amount of aid I've directly or indirectly sent his way. His health problems are unfortunate but his refusal to manage them is not my fault or responsibility (nor is his failure to find welfare or employment), and allowing him to stay here is tolerating an incorrigible leech at best and putting myself at risk of being conscripted into caregiving at worst. I really thought I could help this guy and all I wound up doing was enabling his self-destructive bullshit.
As far as friendship goes (and this is something I'm going to have to work on after this is over so that I don't find myself in a re-run of this situation), I had a bad habit through my 20s of picking up "friends" who really just appreciated my being useful and disappeared/drifted away when I quit loaning them money, fixing their car, etc. If the only thing you value in yourself is being useful then you'll develop a knack for finding people who will exploit this mercilessly, and this roommate is merely somewhere between grandfathered in from the past and the worst case of all of them. It has to end, and I am not obligated to let this guy stay at my place until he dies because of whatever went wrong in his life that isn't my fault.
To be honest, whatever pity or desire I had to help him at this point has been overcome by disgust, at him for his shameless freeloading and refusal to even try and get his shit together and toward myself for having tolerated it for so long. I will not let anger get the better of myself when dealing with him but I cannot and will not continue to tolerate this. This won't be an ultimatum or intervention, just a statement of fact: "You need to leave."
Read your previous posts, you're making the right decision. Good luck.
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I've seen your type before and I'm glad you have identified the problem. Many people are looking to exploit other people. The good news is that when people who have always focused on helping people focus on themselves they become dangerously competent.
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You've got this man! Stand up for yourself! Get this guy out of your life, value your own!! Cut him out without mercy. Any kindness or wavering will be used as a splinter to reinfect you.
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