I would make that dependent on the one hand on which technology the people use with whom you are mostly on the road and on the other hand on the purpose. I run CB and 2m / 70cm HAM. Here in Europe, many off-roaders and overlanders are still on the road with CB radio, so it always makes sense to have a CB radio on board, especially in groups. HAM is (here) more regulated and requires a lot more preparation, learning and an exam to pass. But you have more possibilities with that, more range, useful technical stuff like APRS and so on.
Furthermore (overland) communication is much more than CB and HAM of course. There are so many possibilities and every has its reason (radio, cellphone, satphone, gps messengers and much more).
I recommend you take also a look at the sub-forum
Overland Communication here as there is plenty of information about this topic and many OB members are happy to help and we have some experts here!
Cheers, Bjoern