Helo,
I'm not sure I understand all of the requirements you've listed but I think I'm trying to do the same thing but using Identity Cloaker instead of Witopia.
I have the following:
- Synology DS210j
- NETGEAR GS105
- Motorola Surfboard SBG901
- Identity Cloaker subscription
- PS3
- Laptop (his and hers)
- and no doubt some other internet devices yet to come...
I've also managed to setup squid cache proxy server on the NAS and my original thought was get the VPN on the NAS and then hopefully anything which uses the proxy would be tunneled. Having read around a little it sounds like I can come up with a much more robust solution.
Here's a link to the post I've put on other related forums:
http://forums.smallnetbuilder.com/showthread.php?t=6017
http://forum.synology.com/enu/viewtopic.php?f=114&t=28299