Scoth42

Ever get recognized on the street or otherwise randomly?

Obligatory Not Dave, but fundamentally there was nothing wrong with Vista itself. The "Vista Ready" and "Vista Capable" programs were confusing disasters that never should have happened because it let machines that were in no way capable of running Vista properly be shipped with it (or upgraded to it). This led to a lot of bad experiences.

It also marked the first big shift to 64-bit, which meant everything needed all new drivers. 64-bit versions of XP and Windows Server had been out for a bit, but they hadn't really gotten mainstream acceptance yet on the desktop. Lots of old, legacy hardware thus stopped working and several major vendors (such as Nvidia) lagged a bit in getting really decent Vista drivers out. UAC also was new, perhaps a little overzealous, which was annoying and could interfere with programs expecting to run as admin like they had since time immemorial. This broke a nontrivial number of corporate asset management and security programs, which hindered its adoption in enterprise. And, lastly, it was some of the first big changes to the Windows interface in ages that moved some stuff around that people didn't like.

In all, if you had a decently-specced computer with new hardware with good drivers, and could handle the re-learning necessary to find some of the bits, Vista was fine. Windows 7 was just Vista's next service pack with even more interface tweaks, it'd just been enough time that hardware and drivers had caught up. Microsoft had long been criticized for keeping a lot of legacy junk in Windows for compatibility, and then when they finally did cut some of those threads and remove some of the bad old legacy people were upset that old stuff didn't run. Couldn't win.