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Trade skill should afaik.
Riding improves caravan speed while Scouting improves caravan leader's sight range to help avoid combat altogether. Tactics improves their combat capability but you are still largely at the mercy of the RNG gods. Medicine can help keep keep caravan troops alive longer when the caravan is forced into combat.
Little point buying upgraded caravan as it only affects the party strength at the beginning. When they die, the troops get replaced with new recruits like any other party.
Unfortunately TW doesn't provide anything beyond the basic tutorials and most, if not all, guides on caravans are dated so they may not be up to date.
Caravans aren't supposed to go looking for trouble. As far as I can tell the more combat-effective expensive version of the caravan isn't significantly less fragile than the normal kind (so save your denars). I do, however, like my caravan leaders to be combat proficient, and usually make sure they have good ranged weapon skills and good recurved bows.
At the best of times I've found that caravans eventually get put out of action, so you need to keep their expenses down and their revenue up. Trading and steward skills are really important. I suspect that good tactics skills might make caravans more likely to survive, but I haven't (yet) found a companion with good enough tactics skills to get excited about. So far I've been concentrating on setting up a good route for each of my caravans that isn't likely to overlap with another of my caravan routes.