Don't know if this helps; In 2012 I bought a Caterham from CT that was registered with a CT issued VIN# in 1998 so it was possible then. It's also the same VIN # used currently registered in MA. It had bumpers that were required there (as the only change) but I did not need here. When I looked into the CT process at the time it seemed straightforward compared to what I faced here. You might search this site, I think someone else registered a Caterham in CT not too long ago, they expressed an interest in the bumpers I removed. Good luck
Eric