Snow Leopard Ugrade Nightmare

I dumped my last Windows box well over two years ago, which means the pain and suffering of OS upgrades were, unfortunately, a distant memory when I pulled Snow Leopard out of its plastic sheath last Friday. If I had flashed back to those horrible days of endless backups, clean reinstalls and upgrade utilities that did nothing like what they were supposed to, maybe I would have thought twice.

But every upgrade of OSX to this point had been painless, or nearly so. Stuff broke, certainly. But fixes were easy. And I thought that's where things were headed when I tweeted the following Friday night:

Went to Snow Leopard, and so far so good. New VPN support is killer (goodbye flaky Cisco client). Also, +30 GB of space. Nice work Apple.

What I didn't know at the time was how badly my dev environment was hosed. MySQL was working, but wouldn't talk to Ruby. My Ruby gems were completely messed up. Rails was throwing completely bizarre errors, and lots of things that should have gotten upgraded seemingly didn't.