I still have Windows 2000 installed on a Digital Ultimate Workstation (2x Alpha 21164). I turn it on every few years when I need a nostalgia kick ;-)
In particular, it would be nice to have userspace programs be able to take advantage of new/larger registers without requiring the OS kernel to support the extra CPU state. If the firmware (which presumably is available as soon as the new CPU ships) handles the context switch, then the OS kernel doesn't need an update.
L4/Alpha PALcode was limited to specific set of CPUs it was implemented for, so unlike VMS, NT or Digital Unix PALcode it wasn't available outside of those few machines.
Interesting Raymond continues to mention NT/Alpha now and then. If you run into him mention I have a collection of NT/Alpha artifacts and anecdotes he might be interested in.