I’ve been looking for a reasonable way to get me and my motorcycle to Europe and back (rentals of my bike are $300/day, and I want to ride off-road occasionally, which isn’t great for rentals). I’ve also always wanted to sail the ocean. This could be a win.
Often when you see people on TV doing "around the world" stuff, they actually buy separate motorcycles for each continent, often moving accessories and such over to the next bike. Given the logistical costs for such endevours, the extra bikes are not a big deal and bypass most all the registrarion/insurance issues.
I’ve considered that too- particularly for riding Asia. I do wonder the logistics too of a foreigner buying a vehicle and getting all the paperwork in line, and selling it then; but it might still be easier and cheaper on the balance
I regularly see groups of riders with European plates on their bikes, traveling up and down Highway 1 - a very scenic and twisty road up the California coast. So, it must be doable without too much problem.
Bear in mind that US cars are designed to cope with poor quality fuel with sulphur in it. Bringing an European spec car with engines not designed for use in the US may result in expensive damage.
This is based on what I learned 30 years ago so this may be out of date now.