1) You don't have to buy new.
2) If you've never taken a bike apart before, take some pictures so you'll know how it goes back together again.
3) Working on bikes is not as hard as it seems - get some decent tools and a manual (see the post above about the bike co-op).
4) Clipless shoes and pedals are fine; so are regular shoes and flat pedals.
5) N+1, baby. N+1.
6) Buyers remorse happens. Learn from it and move on.
7) The perfect bike is the one you'll want to ride.
8) 5 different people will give you 8 different opinions.
9) There is no correct answer to the following dilemmas: Steel v. Carbon v. Aluminum; Campagnolo v. Shimano v. SRAM; Lycra v. Wool; Bicycle Brand A v. Bicycle Brand B.
10) Bibs are your friend; don't worry about how you look.
11) Be good to your mechanic; he will save your ass one day. Bring him beer at least once a quarter, if not more frequently.
12) Ride your ride.