Nah... Windows never gets vintage. It's just old and clunky. ;-)
In order to be "vintage" in retrocomputing terms it'd need to evoke a different time. Windows 2000 is... just Windows, but with less bling. It's not like an Amiga, with its idiosyncratic OS, or a BBC micro, booting up to a menu of what ROM's were inserted in the motherboard sockets. Or even modern zOS, which workflows that are kind of based on stacks of punch cards and tapes, even though both are virtualized and abstracted into tiered storage and everything runs on freakishly fast hardware.
Windows 2000 evokes a time when Windows was still enjoyable, or at lease useable. File Manager made sense, the UI elements were distinguishable enough that it's easy to tell what you're doing, the look was consistent. Definitely nostalgia if you use Windows 10.
In order to be "vintage" in retrocomputing terms it'd need to evoke a different time. Windows 2000 is... just Windows, but with less bling. It's not like an Amiga, with its idiosyncratic OS, or a BBC micro, booting up to a menu of what ROM's were inserted in the motherboard sockets. Or even modern zOS, which workflows that are kind of based on stacks of punch cards and tapes, even though both are virtualized and abstracted into tiered storage and everything runs on freakishly fast hardware.