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This. Exactly this!
This is the allegory of today's generation.
Check your inventory and dump some dragon bones on your follower and/or grab the patch. It's well worth it even if you don't intend to mod otherwise.
Bethesda had to do this for the Special Edition release due to it being on consoles and them having a contract that stops achievements with mods. Been in since SE got released. You can unlock them again with a simple mod though, one version requiring SKSE64 the other doesn't. There's enough threads with links so not bothering to post yet another.
With the carriage, are you using Immersive Citizens? I had major issues with carriages when I installed that mod due to either conflicts of incompatibility with other mods I was using. Back in November'ish though, so it might be better now. I still won't use it.
Otherwise, as before, are you using the Unofficial Patch? And you are paying him first, then sitting in the carriage after choosing a destination? Also, what mods are you using? There might be a script hanging somewhere due to load order issues that is interfering with the driver.