if you've got the latest zen firmware version (2.20.05) then it'll definately work with MC 11.0.316, well at least mine do
have you tried resetting the handheld options so you get prompted again for all connected devices?
when you plug it in do you get a system tray icon, showing that windows can actually see the zen?
2.20.05 is not the latest firmware. Creative have done a good job in confusing the hell out of everyone it seems.
V2 includes support for Plays For Sure but does not include many of the fixes that were implemented in version 1.11.01. One of the fixes in v1.11.01 and not in v2 is the reduction in the time it takes for the unit to go into a full shutdown from idle standby. Many v2 users will find that battery life is reduced significantly because v2 is 12 hours (i think) and v1.11.01 is 4.
This is why many users, including myself, that have no use for Plays For Sure have not upgraded to v2.