I've always been a believer in the phrase: If you can't fix it you don't own it. The concept follows that in reality you're really just renting your bike from the repair guy.
A bicycle work stand is handy even when just washing a bicycle. The work stand was the first bicycle specific tool I bought. Then I got more. At first I borrowed a bicycle repair manual from the library. Then I bought one. I also attended a bicycle maintenance class at the local performance bicycle shop. I hung around the bicycle co-op where bicycle knowledge is shared for free. And I still watch lots of the bicycle videos on Youtube.
I've bought old but still valued 10 speeds off Craigslist for winter wrenching projects. I've found I really enjoy working on bikes.