I clean my wheels and brake pads after every ride because I ride on some pretty crummy roads. I also wipe down my chain and wipe off the jockey wheels after every ride. I lube the chain and grease/oil/lube every 250-300 miles and clean the chainwith chain cleaning solution and relube it, every 500 miles after I clean the bike . As far as lubbing the none chain parts, defintely anywhere metal touches metal should be lubbed this includes where your cables go through the mounts on your bike, and where they enter the adjustment barrel, the center of your jockey wheels (the two cogged small wheels on your derailleur) the pivot point on the brakes and several other points that seem to need it.

Like NY biker, once a year or whenever I finish a cross country tour, I pay the bike store guys to take the bike aprt, clean it, relulbe and regrease everything and reassemble. Depending on the mileage, I may get a new chain, derailleur cables or brake pads as needed.

Bebe my Trek 5.2 pilot is 6 years old and has over 50,000 miles on it so I guess my system works. But then I am also a bit compulsive because I ride alone out in the country, no stores, no taxis, often no cell phone coverage, and cannot afford to have something go wrong with the bike. I also do the 7 point check before I ride- every time.