With about 3000 abusive miles on my drivetrain, I'd shot my chain and worn my cassette. Starting my second summer as a commuter, I figure I ought to learn how to do it myself. Arrogant and ill-informed, naturally I made some mistakes, so now my goal is to figure out what I should have learned from them. Hopefully someone here can confirm what I did wrong.
With the right tools, the cassette was easy. The chain was the problem.
I bought a cheapie Nashbar chain, figuring it wouldn't cost so much to replace when I screwed it up. (The only thing I did right) The chain came with a two-part master link that I can use to put the chain on and off without tools for cleaning. In my wisdom I said screw that, I'll just drive the pin mostly out, and then drive it back in to reconnect the chain. -- was this my first mistake?
[This is the part where I got really stupid]
So I measured and broke the new chain at the right point. So far so good. I thread the chain through the derailleur and drive the pin back in to reconnect. And realized I'd threaded it through incorrectly. So I drove the pin out again, threaded it through correctly this time, and reconnected. Only to find I'd gotten my derailleur cable housing on the wrong side of the chain. So I drove the pin out again, and _finally_ got it right and reconnected the chain.
I take it for a spin around the block, and things seem to work well. The next day however, my first time through an intersection I bear down and bust a link on the chain. So the question is, did I damage the link by abusing the pin so many times, or did I screw up from the get-go by trying to extract and re-insert the pin at all?