Although it was impossible to get important work done over a VPN over Amtrak's Wi-Fi (I really need VPN access for my job), it was still a fun journey from Charlotte to Philadelphia on my way home from a new years party. I worked from home that day, and while I was mostly incommunicado I could still get a lot of code work done on my own machine that I'd been putting off.
Unable to have reliable VPN access over Wifi as you travel across several states? That's hardly a complaint. There's no way to travel that would give you that.
Many Windows-based corporate VPN clients like to tear down the connection on every little net hiccup, forcing you to do redo your SecurID or whatever login. And Windows IP stack likes to tear down your TCP connections on any brief loss of link, so eg. your SSH session cannot survive this type of event.
I would definitely do this.