[flitzwhopper]

I'm a CIO within a few years of retirement. Really just a programmer. My opinion is that NJ might be a bit too cold for full time Airstream living. While the furnace works fine to keep things warm, the propane it uses might be significant. Other than that, there wouldn't be any challenges to your plan. However, if you weren't planning on doing some roving, there might be better solutions to your housing situation.
As to being connected, broad band access to the Internet on the road is pretty straightforward and is getting economical enough to use as a permanent connection.
When I retire, we'll probably be completely "off the wire" and rely on various forms of wireless connections to stay online.