Apart from Fortran at university, I didn't bother with computers until the Boss obtained a BBC Master for the squadron. I taught myself to write a couple of programs for that, including all the current ATP-56 rendezvous manoeuvre calculations.
Then came Win 3.1 which I only used for WordPerfect, although the PC was supplied for us to use for HMI evaluation of a Link16 proposal.
The first laptop I owned used Win95, which was fine. I skipped the next versions of Windows and went straight to WinXP which is also fine.
Win7 doesn't include Outlook Express, neither is it compatible with it. A silly thing for Microsoft to have done as the supposed replacement, 'Windows Live Mail' is truly awful.
As for Win8, advice I've had is not to bother with it.