Windows 7 was by far the most painless OS install I've ever encountered. Ran the install, formatted the drive, waited about 20 minutes, installed video drivers, ran update, finished. Some minor OS tweaking here and there but otherwise very, very simple. I feel that as long as you don't have incredibly ancient, or bleeding edge hardware, you should be fine with the pre-packaged driver support. If not, Windows update and grabbing latest drivers from hardware manufacturer websites are easy enough, with the latter possible to prepare beforehand.
Back to iPad, I have friends who bought or were given iPads and after the novelty wore off they've been largely unused of late. I don't see the appeal of a $500+ paperweight. I've also yet to see one in the wild here in NYC.