Decided to make this guide since I seemed to avoid playing Caravan like the plague because the concept seemed so confusing and time consuming.
So here we go, you can do this without any in depth deck building, you will merely need to eliminate the Queens, Aces, and Jokers from your deck as they are pretty much useless (at least in my experience) you will only need to do it once so after you do that you are set for 30 games. What you need to do is travel to Novac and find No-Bark since after he loses all his money he will just play for free so this is just easier.
Now for the rules of Caravan. The object of the game is to get your stacks as close to 26 as possible without letting your opponent do the same. I usually start my stacks as a each different suites starting with a low number card if possible.
Break down of cards:
Number Cards - Self explanatory they add up as your would expect
Kings - Double the card you place it on. So for example you have a 10 card placed down putting the king on it will bump it up to 20. This can work in your favor in two ways one giving you a high number for your stacks, and two using the King on the opponent stack to make him bust.
Jacks- Remove the card it is placed on, great for messing up the enemy caravan or removing a king your opponent has placed to make you go bust.
Hopefully my guide helps as I was able to tackle the achievement in about an hour of gameplay, I also highly recommend saving after a few wins just in case the game decides to lock up on you. If you have any more questions or need more tips please let me know this is my second attempt at writing a guide and any and all feedback is appreciated.