Finally had a chance to circle back on this with you guys. It was a fantastic road trip and #1190 is very happy in her new home. The roof stays in the trunk (I actually use the roof bag so it stays clean b/c I know I won't need it very often). And we had a very successful relocation from Chicago to San Diego. To anyone thinking about moving your roadster on your own - I'd highly recommend it. Use the tips that our compadres said above and be cautiously optimistic as you motor along your way.
Enclosed are some pictures of our adventure!
Pulling up to the U-Haul trailer with an amazing crew that helped us SO MUCH. Notice this thing called snow that we won't be seeing again any time soon! We actually broke both of these particle board slabs when we pulled the car up - but we got it up!
Our H-Haul helper tying #1190 down - notice how tight he did it on the front. So much help these guys were!
Safety chain that he wrapped around the axle - I knew that this was not optimal, but there was little other choice unless we wanted it dangling.
Filling up late night outside St. Louis, Missouri - I took these pics nightly, just liked the irony of it all!
Worlds Largest Gift shop somewhere in Middle America, Oklahoma with #1190 being a bit of an attraction in and of itself
Taking a spot with the big rigs in Amarillo, Texas outside of a true steak house ranch joint (featured on Man vs Food)
Clines Corner in the middle of the Texas/New Mexico Desert
Finishing a day of driving in Albuquerque, New Mexico
Stopping for lunch with my girlfriend and our little pooch somewhere in West New Mexico
Finally arriving in El Centro, California to get #1190 off the back of the truck (120 miles to go to get to SD). Look at this awesome slope that we could use to unload the Roadster. It was almost flat by the time we pulled it off. Again, U-Haul staff was awesome here. #1190 loved the remainder of the drive from El Centro to SD. My GF did the drive with the top down and our pooch hung with her. I followed in a much more nimble U-Haul.
GF and pooch getting ready to head out
Charging at my dad's Nissan Leaf charging station in his condo's parking garage downtown San Diego using The Can J1772 adapter (a must buy for any Roadster owner).
All in all - everything ended great! Hope this helps anyone thinking about hauling a Roadster themselves.