Just to add my two cents of nonsense from my two-bit memory banks, I think that the biggest bane of Windows is that $&&@&$!! registry. When you uninstall a piece of software, the uninstaller typically does not remove all the registry keys. For that reason, I almost always run a utility called File Cleaner to clean up all the stray garbage.
As a recent returnee to the Mac World after a long apostasy to the Dark Side, I have been so pleasantly surprised at how easy it is on my new Mac Mini. I have it set up as a dual boot system, with a small amount of real estate devoted to Win 7. My wife always knows when I am "on that side of the house" by the change in vocabulary that comes from my study! When I boot up the Mac OS, I'm sure I always wear a grin. But when I uninstall something, I still have that uneasy feeling that I still need to do some cleanup---until I remember that I am on a Mac.
Of course a bit MORE flexibility for file transfer on the iPad would be nice. It is just a little TOO spartan.