-Sabotage the other player's caravans by overburdening with Kings.
-Sabotage the other player's caravans by dropping Jacks to scramble or reset their sets.
-Sabotage with a Joker off your set to reset the opponent's set across from yours. Too bad you have to remove the Joker-tainted set from your field because you can't play anything off them.
-Reset your suits with a Queen if you're low on cards of one suit.
-A caravan of 21-24 with an Ace in it gets "sold" easier than with different cards.
-10+K+6=Easy 26.

This worked for me about 2/3 of the time. Finally got that Caravan Master trophy out of the way and made 30K+ caps too. The rest of the time, the first three strategies make for a rough win for your opponent. Imagine if Obsidian gave the AI enough power to do the same deck damage to you, you'd never win. The computer just scrambles to easy 21's or 26's with high cards most of the time, thankfully.

Don't bother with jacks or jokers, just have a lot of kings.

Don't bother with anything but kings, 10s, 7s and 9s.

Ideally you can have a turn-6 win every time. 10+7+9 = 26.

I don't waste time building decks before I play. I like to just have a ton of cards to draw a good random deck from and play clean and for fun because I always have 10K's of caps anyway. Even card sharks like Ambassador Crocker, that Gun Runner Guy, Canyon Runner, and Cliff Briscoe can't win all the time.