Write apps. Deploy them.
I learnt most stuff for myself. Eventually I got into #caboose and was able to ask a lot more questions directly to the people that wrote rails + the plugins I used.
I enjoyed finding fun aspects of ruby and making little gems from them, e.g. Magic Models.
MyConfPlan - write tests. Hobo was great and I wrote the app fast, but when it started failing I had no test coverage.
Make my own tools. TextMate bundles. GitHub command line tool.
Deployment. Took me a very long time to figure out deployment. I also didn't feel I had to pay for monthly slices, so I suffered trying to deploy to TextDrive shared hosting.
mid-2005
Straight to Rails
Rails Recipes and Advanced Rails Recipes
OS X now, I used Windows XP for 1.5 years
TextMate, though I used RadRails for 1.5 years when I was on a PC