So after a million hours of contemplating, trying out everything in the thread I posted last week (thanks to everyone who replied, BTW) and a couple frustrating hours of cable mess, I ended up with this:
Routing, for routing nerds:
Freeze > Green Line > Feedback Looper
FL Send > Death Metal > Digilog > Swollen Pickle > FL Return
Fuzz Factory > Big Muff > Red Threat > PH-3 > Rainbow Machine > DS-1 > Memory Boy > Carbon Copy > Ditto > DOD EQ > Dispatch Master
It sounds fucking ridiculous, works for the band and for my solo work, and is generally fun to play around with. I think it'll stay this way for awhile. Or at least until I buy the next pedal I can't afford.