I've dipped my toes in the water of Linux, and boy does it get frustrating after a certain point. I've grown up with Windows, gotten more or less intimate with the ways of tweaking things, installing software, etc.
Starting fresh on a Ubuntu installation, I found that there were a lot of itty problems that popped up here and there which required far more expertise than I had. On Windows, I can generally power through those problems with my knowledge and experience, but on Ubuntu...
Getting my printer to print, for example, was possible only through extended commandline manipulation of the drivers of other printers. And I still couldn't get it to scan. Now this isn't the fault of Ubuntu, it's the fault of the printer manufacturer, but still, an OS-specific problem.
Another time, post-automatic update, my sound didn't work anymore. Sound is important to me. Extensive driver manipulation on the commandline again. I'd grown used to having a GUI for everything with Windows, but for even ordinary manipulation of operating files, I found I had to look up a variety of commandline options. I don't think they let you right click on a file and press "Run as Administrator" for anything. I had to go into commandline and SUDO away to touch any important files, like the GRUB menu list.
Getting Ubuntu and Windows on the same computer was no fun. They do NOT get along well unless you lay down some separate partition groundrules. (I originally installed before I knew of WUBU, which made everything a hell of a lot easier.)
1st time: preexisting Windows, Ubuntu hijacks main partition, kills windows. had to nuke both to fix.
2nd time: Install Ubuntu first, windows won't install, detects another operating system? nuke, try again
3rd time: Install Ubuntu on separate HD, remove HD, install windows on another HD. SUCCESS
Later I just nuked everything, installed Windows and used WUBU to install Ubuntu. Much better.