I don't even see a problem with insurance or licensing.
To be sure you can call or email Grundy or Hagerty and explain what you are going to do and see if they would have any problems insuring you. I have taken a 2,000 mile road trip in one of my collector cars. I'm with Grundy. Although their policy states that the car is to be kept in a locked garage, they had no problem continuing the insurance when I called them and explained the trip I would be taking.
Also contact the state(s) that you are thinking of purchasing the car in and ask them about licensing (in the US, every state has different laws relative to registration and licensing).
I think it might be good to get 1-3 others interested in doing the same with you. Either fellow countrymen or folks from here. A big group would be more trouble than it's worth (MHO), but a few might make it more fun, more interesting, and safer.
I think a max of 200-250 miles a day would be my target. The car can probably do more, but I may not be able to
. This would allow for stops at interesting spots, and an early end of the driving day to relax, service the car (and maybe have a beer?
). 6 weeks would be plenty of time to shake out any problems in the "new " car, do the 3,000 miles, and sell it at the end of the trip.
It would be great to live blog the trip. Another good reason to stop early in the day...to write the blog entry. By doing so, you may have a line up at your destination to purchase the now famous Model A.