Like art and gravity, "rock bottom" is subjective. One person's
lying nude in a pile of their own used breakfast is another person's B
minus in meteorology, so you really have to decide for yourself when
it's time to flush your stash and board a bus to Provo.
Good signs of rock bottom are self-loathing, eviction notices and an
urge to watch non-stop Nick at Nite.
Reinventing yourself is something you do after a bad breakup or when
you've grown weary of being the town whore. Reinvention is more about
superficial changes rather than any actual introspection, so it's easy
if you have access to a bottle of Nice n Easy and/or a fake Canadian
passport.
If your reinvention doesn't work, you can always move to Provo.
The grass is always greener, which means no matter what choices you
make in life, a career in finance or reconstructive dentistry, getting
married young or celibacy, you're never going to be happy. Feeling
like you're missing out on other things means your S-class won't even
make you feel superior to everyone else the way it once did.
Try keeping another family in Provo, a gender change or developing an active Second Life to get the full life experience.