I think I know the answer is "No".... based o experience with Server 2003 at work... but it seems worth asking.
Is there any way to have files in a WHSH share go to the TrashCan when they are deleted by a session on another PC?
Right now, if I delete a file while logged on directly to the WSH box, it dutifully goes to the TrashCan.
But if I were to delete the same file from a PC that's just going at it through a WSH Share it goes straight to the Great Bit Bucket In The Sky.
Ouch.... OTOH, it's the same behavior as at work where the pros are administering Server 2000-something.
As kingslaye505 said, no. And also, as you've noticed, that's not a shortcoming with only WHS, but with all Windows shares in general.