For background - I'm a hard-core Unix Administrator (professionally) for the last 15 years (supporting SGI Irix, HP-UX, Solaris, RedHat, VMWare, etc...) who's mantra is "GUI's are for lazy people" and approach tasks from the concept of "what can you do when the system is down and you're using a VT term".
However, as much as I hate to say it, each time I try switching my home systems to Linux there is always something seemingly simple (in Windows) that after days/weeks researching I can never get working, so I go back to windows. Wi-FI? Forget it. Winamp replacements to listen to streaming audio? Forget it. Gnome3 desktop on dual monitors to work right? Forget it. Yes, I've tried lots of different distros, but I always eventually find SOMETHING that I can do easily on Windows that I can't do with Linux (and lets not even talk about games).
I can't even imagine trying to explain to a novice about device drivers and how to find, install, and make sure they work. Oh, you are trying to get your WiFi/Sound/Video card working? No, you have to search by the chips it uses, not the brand name. How do you find that? Depends on the distro which tools you can use. How do you add new software? Well, check your dependcies ("What are those???"), make sure those and their respective dependencies are installed ("How? Depends on your distro what tools it has...") and then install the app you want. Oh, it requires a kernel patch to work?
Gimme the damn Windows install disk.....