Also, instead of buying everything new, develop relationships with cyclists in the area and buy good quality used stuff with lots of mile left in it for a small fraction of new.

And don't sweat working on it yourself. You'll strip bolts from time to time, you'll ham-fist something and snap it off, you'll forget to snug the brake cable and and have to stop by dragging your feet. We ALL did that. But lord's sake, John, "I'm klutzy - I have no luck with anything mechanical..." I say to you: Reach down, nut up and grab a damn wrench already. Not trying is a much worse failure than breaking something or snapping a cheapo plastic fender that was never expected to be removed (most bikes in America go 5-10 miles and rot in a garage for the rest of their time).

Oh, and check the library for bike books before you go shelling out money for the same title.