Debian is awesome for intermediate/advanced users. I started off with Slackware 8.1, and it was kinda tough because you really had to do everything yourself. I have Debian installed on my machine, and I dualboot with XP. I actually had to compile my own kernel to get sound to work automatically, though. After all of that It still gives me fits. Running bittorrent and any form of IP blocker available for Linux causes my system to lock up or slow to a crawl, so I've benched it as my main OS for the time being. I still do my CS homework on it, though. It was a great learning experience, but definitely not something someone should just try to jump into.
So I guess I don't have any advice, since I do things the hard way most of the time. One thing I do want to recommend, though, to people who want to customize Windows more: Litestep. That URL is the one place I know it's always available, but it requires registration, so...that kind of sucks, I know. It's a different windows shell, easily customizable for someone familiar with how computers work, and runs faster in my experience than Explorer does. It's great, and it is really easy to switch back and forth from LS to Explorer again if the need arises with the tools that come packaged with the installer. Everything that runs on Windows runs totally fine on LS, as far as I know. I'd post a screenshot of my current setup but...it looks almost empty. Just a taskbar, virtual desktop manager, and a clock. Everything else is managed through mouse-driven menus.
So I guess I don't have any advice, since I do things the hard way most of the time. One thing I do want to recommend, though, to people who want to customize Windows more: Litestep. That URL is the one place I know it's always available, but it requires registration, so...that kind of sucks, I know. It's a different windows shell, easily customizable for someone familiar with how computers work, and runs faster in my experience than Explorer does. It's great, and it is really easy to switch back and forth from LS to Explorer again if the need arises with the tools that come packaged with the installer. Everything that runs on Windows runs totally fine on LS, as far as I know. I'd post a screenshot of my current setup but...it looks almost empty. Just a taskbar, virtual desktop manager, and a clock. Everything else is managed through mouse-driven menus.