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vista was just plagued by a terrible release. ranging from microsofts own incompetence to terrible third party drivers, like nvidia's and creative drivers causing a huge influx of BSOD's. if they had released it as its service pack 2 version it would of been far more successful.
from a UI perspective vista today still has the best UI layout and visuals. it also still supports classic look and does so better than 7.
if microsoft released a service pack 3, updated WDDM, and gave its start panel the ability to "pin" more people would of stick to it.
windows 8, regardless if its "enterprise version" or not, is one of the worst from a visual perspective. the matter of needing a third party start menu, to have a start menu, is what puts it on windows me level. how microsoft abandoned their own universal, loved, and known "trade mark" that helped spurred their success is beyond baffling.
10 would be close but its continued focus on flatness, a start menu that barely should be called a start menu (you cannot pin shortcuts to it?? you cannot even easily add or remove shit from the start menu??), and the massive amount of privacy scandals (which microsot has been trying their best to install on both 7 and 8 machines via sneaky updates) makes it close to being another mediocre release from microsoft.