Recently I upgraded my laptop to Snow Leopard. From Tiger. Bypassed Leopard completely.
Stupid is as stupid does.
My reason for making the jump up was simple - there were apps (or upgrades to apps) that I wanted to use that needed Leopard. But Snow Leopard was out, and the upgrade disk I tried for Leopard had failed, so Snow Leopard was tried and upgraded successfully. And now I'm gradually finding all the things that have broken in the process.
Registrations of various apps have gone AWOL. My Fink set-up is broken - I expected that, but it may be a while before a number of packages I want are ready for SL. FruitMenu doesn't work. Spotlight comments have been wiped. Dashboard seems to be completely borked.
Those last few have been the most painful. I had a number of things in FruitMenu that I used more than I realised. Same with Dashboard. You don't know what you've got till it's gone (as someone once sang).
At least I've found a (partial) alternative to FruitMenu that I can live with: XMenu. It sits in the top right corner, so I'm gradually learning to change sides, but it works well.
The Spotlight comments issue is the biggest pain, in conjunction with the fact that QuickSilver (which I'm now addicted to) has some issues under SL, namely that certain advanced options, like the File Tagging module, cause QS to crash. I had been using QS's tagging options to keep a lot of stuff organised. Now those tags (stored as spotlight comments) are gone - %$#@!
I can work around the lack of the File Tagging module to some extent using Automator to add my common tags. But this is quite limited compared to what could be done with QS's File Tagging module.
Still, overall I'm pretty happy with Snow Leopard. And when I get time, I'll be able to find solutions that suit the way I like to work. When you play in the snow, you have to expect the odd chilblain.