pion: What are the permissions on the directory? Non-VM flagged users must have write permission to the directory if they wish to modify its permissions. The "Permission Denied (directory mode)" includes the reason why. The user probably isn't the owner and the mask is 755 or not a member of the group and the mask is 775 or something. Unless the directory is 777 a SiteOp who is a non-owner non-group member who isn't a VM flagged user cannot change that directories permissions. While not specifically applicable the "site perms [<what>]" command might be useful.
I have zero clue about that TCL error. I'll have to poke around but my guess is it failed to start a process for some reason... Server out of memory? Kernel memory? Handles? Check for something in the windows event log around the same time. I've never seen that before though.
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