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My experience with Linux installing has basically been "Install thing I want. Oh, that didn't work. Repeat [Looks like... I'm missing something called [name]. Install [name] and dependencies. Clean up and try installing thing I want again] until it does." Add sudo where necessary. It's not perfect but for some types of software it's several times easier than getting it working in Windows. And yeah, if Ubuntu is an issue there are many other distros with a similar style - GUI friendly, and designed for people who aren't hardcore into *n?x (I am not either). Just a suggestion anyway. I personally really like having it sitting in a virtual machine, and maybe that would work really nicely for you too.


As for win7/win8: having used both, 7 is absolutely better. 8 is basically designed for tablets, and even more so for casual computer users, which means a lot of design decisions that make no sense for a workstation. Think mouse "gestures" where you have to hover in one corner of the screen, native apps that will ONLY run full-screen (including the PDF viewer! what were they thinking?!), and a start screen where your programs are shown in little boxes across the whole screen. I'm sure you could get around some of its problems by getting used to it and overriding a lot of the defaults, but I don't see why you should have to bother. Get the one designed for real computers and save yourself some hassle.

Full disclosure: I still have XP 'cuz I'm lazy.