The only pain I see is routing through the VPN once set up. You could either use UDP over VPN to do dhcp from the VPN server and set the route that way, but then you have to be careful not to lose your route through the wireless router.
I've thought about taking this approach to wireless security and this is the barrier that has prevented me from trying until I have enough ambition. I also share my wireless with a few people and wouldn't thrust upon them the need to manually set up routes each time they connect. Von Fugal
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