Don't know about 64bit windows but 32bit should work, we use it on several machines, under citrix on w2k3-terminalserver.
1. Of course server needs to be in installmode :0)
2. apply a policy via gpo to outlookconnector-users in group/container 'zimbra'
3. start up outlook en fill-in the settings.
This should work, every users gets his own settings en .zdb-files. We put them next to their profiles on shared storage so they can be accessed from any server.
Hope this helps,
Using ZCS Network-edition 5.0.16 on Ubuntu 6.06.2 LTS and 8.04 LTS