Even though your train of thought sounds very complicated (had to re-read it more times than I'd like to admit..), the core of it is a very sweet advice. I know where you are coming from and it seems to me like you have all your shit together, which is fantastic!
Unfortunately for me, my brain is my greatest enemy, throwing sticks at my feet every chance it got (that scumbag!), making me feel miserable for so many things (not just guilt). I know that I should find happiness within and not let myself be controlled by what society dictates, but that notion is just so deeply seeded inside that it is hard to ignore. But I digress...
What I wanted to say, is that the guilt I feel is mostly over losing contact with friends that made me actually feel really happy in the past which is something that I can only say about a fraction of people surrounding me. I guess I am just trying to convince myself that I can feel that happy again if I revive the relationships. Maybe I will, maybe I won't - I guess only time will tell...

Daamn, what a load of mortal coil :D Thanks for sharing your opinion, this was one of the best interactions I had today (including real life)!