Hi Matt, I have two greys, a TAG and a CAG. My Tag, Ana Grey, is 6 and very mellow. She loves everyone and is not a fraidy cat. She would be a great trucker's companion. Now my Cag, Sterling Gris is 3, he is afraid of every new person and everything. He puffs up real big to scare off the "the bad" humans. My youngest daughter and I are the only ones he trusts. Both birds I have had since they were weaned by their breeders. Both were raised by me under equal circumstances. I guess what I am saying is that it all depends on the personality of the grey you choose. Ana Grey's breeder made sure that she knew about nail clipping, bath time, and time with the human parront from the time she was weaned until adopted by me. This person was a great grey breeder. Sterling Gris' breeder was not so concerned. Sterling Gris, however, is a great talker and learns very quickly. He would be a great companion as he loves to sing and talk but shrieks like a banshee if frightened.
I believe with proper research and taking a young grey on trips with you from the beginning would be very enjoyable.
Both of my greys are fully flighted and microchipped and registered with Homeagain just in case they should go on an adventure without me. Good luck.