Thanks SpaceBass for the validation that VPN is the way to go.

Just wanted to clarify that the $20 Buffalo home router with DD-WRT has a full OpenVPN server implemented (including the push "redirect-gateway def1") which routes all internet traffic through my home ISP.

I was hoping if I could trouble you for a sanity check in my network as I'm a relative newbie to Linux & don't know anyone savvy with Ubuntu or OpenVPN.

This is weird, but my setup is:

[Cable modem] --- [Buffalo Rtr] --- [Switch] --- [Ubuntu server, home machines, etc.]

I have two OpenVPN servers running on this network...the Buffalo router AND the Ubuntu server.

The router is running OpenVPN as TCP on port 443.
The server is running OpenVPN as UDP on port 8080.

Normally I'll connect from a hotel to the server -- UDP runs faster & gets very few disconnects. The reason for the router is that I've been at some hotels that block port 8080...some even block UDP entirely, ugh! - no Skype, YouTube, etc. My thinking is that they can not block TCP HTTPS traffic without completely crippling the usability of their internet.

Overkill or healthy paranoia? Opinions greatly appreciated.