If you like being in his life, then what's the trouble anyway?
I missed this part of the question (or subconsciously ignored it, who knows

)! My gut reaction is to tell you how concerned I am for this man’s well-being and how I want to see him have less trouble in life (he has difficulty holding down a job, place to live, and has run-in’s with the law time to time), which don’t get me wrong, I do! But, to be completely honest, there seems to be more to it than just that.
He reminds me ALOT of how my dad was (except my dad’s behaviors were much more self-controlled compared to my friend’s chaotic nature) in terms of charm and manipulation skills. My dad never got any real diagnosis before committing suicide several years back (except of course depression, which was only a piece of the puzzle in my opinion), but after stumbling upon this forum, I’m starting to see many ASPD traits in him (I initially thought bipolar with him as well).
I guess I would have to say that deep down, I am also looking for answers for myself, and the more I learn about ASPD in terms of symptoms, research, possible causes, possible treatments, ect, the more I am able to form connections about the relationship between my dad and I, possible genetic influences, and the effects it has on me now (I have and experience strong emotions when it comes to relationships with others; only problem is they scare the F**K out of me, because there is no logic, rhyme, or reason behind them......they just pop up out of the blue and tap me on the shoulder when I least expect them!). So instead of embracing them like “normal” people do and enjoying them like many, I reason my way out of them, bury them, lock them in closets and hide the keys, or whatever is necessary to restore order in my life. OR, my recent discovery looking back on life, I find emotionally unavailable/limited individuals to connect with; which is not as scary because their needs are low (ask any “normal” man who has encountered me and attempted to pin me down and they would describe me as: “flitty”, “wishy-washy”, “hot and cold”, ect). In addition to the emotional aspect of relationships, I become intrigued when there are games involved, and the more skilled a person is at games, the more appealing they become (my end goal: to win of course!).
However, as fun and frightening as all the above may be, it is not the way I want my life to continue forever. I do want to have meaningful relationships in my life, one’s that are not superficial in nature and that do not involve “one up” games. I want answers to certain questions, and I want to find a path that will fill the voids I currently have in my life. Additionally, this area of psychology (various personality disorders) is very intriguing to me, and I would like to learn more in order to possibly expand my career into waters that are still, to some degree, uncharted.