>>1
Either get a mac if you've got the dough, or put a bit of effort into learning linux. Suse and Ubuntu are a few of the easy to use distros, with GUI/automatic installation.
For all your advanced linux questions, either check out guides and how-to pages on the linux documentation project
http://www.tldp.org/
or ask questions on a linux forum.
http://www.linuxforums.org/forum/ is pretty good. They have a newbie section which you can search through for answers, or post your own embarassing question. People are generally pretty nice. They also have distro-specific forums for localized problems.
I personally use a mac, since I needed a laptop with good hardware, and a hassle-free interface, but linux is a perfect alternative, especially if you have a desktop already. I recommend giving one of the aforementioned distros a spin. If it doesn't work or suit your tastes, try another one. See if you like KDE or Gnome better (both are now supported by Ubuntu, by the way), and if you still think it's a bit too technical, get a mac.
A word of warning though: if you're into gaming, windows or linux with cedega is still your best bet. Despite the new macs being x86 based, I don't believe Cedega or Wine runs on them.
Good luck exploring this brave and sometimes slightly frustrating new world. In the end, it's still much more relaxing than running windows, most of the time.