Just to jump in, since you asked what Tripoli means to people...
Re-listening now. Heh. This is my all time favourite. It basically got me into Matt Good. I was sitting at a friend's house, and she had a random mix CD, and I heard this song on it while we were chatting and just said "Wow, what the hell is that?" Since then it's become something very powerful for me. I was on the verge of tears when first listening to the acoustic on Rooms.
I hear it differently than, it seems, most else do. To me it's a song about rebirth. "Where has my head gone..." I see as someone looking back on their life and going "What was I thinking?" Maybe looking at their friends and being surprised they're still there ("Do you hold up..."). Then finally the character feels all the idiocy, all the bad things that have gone on slip away, and he's reborn. I guess I just see the song as so...powerful. Not really upbeat, but sad in the way of like...a breakup that is for the best. Or something that hurts you deeply but only makes you stronger.
That's how I see it anyway.
-Tom.