I was very seriously considering this. I originally wanted it done really close to the shutdown, but after some research that proved improbable at best.
First, winter is the worst time to do this because the upper level winds are insane, meaning you could end up with a 500 mile trip to retrieve the vehicle after it comes back down.
Second, I'm uncomfortably close to the east coast of the U.S., and the risk of an ocean landing is too great.