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My general rule of thumb is to avoid every other version of Windows.
8 -- I can't comment on it yet, but if the pattern holds, I'll avoid it as long as possible.
7 -- great
Vista -- bad
XP -- good
ME -- very, very, very bad
98SE -- good, what Win98 should have been
98 -- bad
95 -- good
... the pattern holds.
Obviously, based on the list above, WinME is my candidate for "worst version of Windows".
In addition to the "every other version" rule, Win7 was the only version that I purchased before Service Pack 1 came out. Maybe when they roll out Win8 SP1, I'll think about it.
3.11 for Workgroups - bad
3.1 - good
Presumably, 3.0 was bad, 2 was good (or at least good enough to make Apple try to sue Microsoft over the "look and feel" - sound familiar?), and 1 was awful. However, I don't have install disks for 1 or 2, so I can't verify (I remember 3.0 being pretty bad compared to 3.1, though).
Also, there was a bit of a subversion to this pattern in the NT family tree; NT 3.1 and NT 4.0 weren't great, while Windows 2000 remains my favorite version of Windows ever.