This is something that has always bothered me, from the start of the game. The courier's just some dude in plain clothes that runs from one end of the land to the other. He has no weapons or armor, and probably has no spells or abilities.
The caravan driver's a polite dude in plain clothes with no weapons or armor. As his primitive vehicle rattles down the unimproved roadways, he has no idea what's creeping up behind him.
A level 25 Dovahkiin that is fully armed, armored and fully prepared for danger can still easily get his butt kicked.
I was just wondering, why doesn't the caravan have a few armed people aboard, or why doesn't it at least have an armed caravan escort... and why doesn't the courier ride with one of these? Surely they'd perish otherwise, in just a few minutes, in Skyrim's savage wilderness.