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Caravan is a great way to make some easy caps in Fallout: New Vegas, but it's a slightly complicated game for new players. To start with, note that PC players have to play the entire game with their keyboard (this seems to cause a lot of confusion).
Note that if you really don't like it, you don't have to play it. Normal gambling in the Casinos will also allow you to make money. You should get a full set of cards all on your own after you are introduced to the game by Ringo in Goodsprings. You can buy new cards from many different merchants in the game. Each of the main casinos has a deck of cards available. Note that these don't really change much other than the look of your deck. There was originally a bug in which purchased cards merely went into the players miscellaneous inventory instead of being entered into the deck. Dropping the cards and picking them back up should work, or you can sell them to a merchant and buy them back.
The actual goal of the game is simple. You place a bet and the winner takes all. You can raise any amount, but the pot will only go as high as the other person commits. The goal is to form three tracks of cards, representing three different caravans. From a conceptual standpoint, they need to be loaded with enough goods for a profit but not enough to be overloaded. This means that each of the tracks has to fall between 21-26. If you go over 26, then the track is busted and you'll need to remove a card with a Jack or Joker to fix it or discard the entire track.
Aces are low and face cards don't have any value. Kings, Queens, Jacks and Jokers only have special impacts on the cards. They can also be played against your opponent's tracks to mess them up. Since the AI doesn't seem to be able to use face cards against you, this is the easiest way to gain an advantage.
Update: I had thought that they had patched out the bug causing caravan players to not actually bet anything. Apparently some people are still having problems with that. Unfortunately there doesn't seem to be much that can be done to "fix it." I just suggest that you try to play caravan again with a few different opponents and hope that the script gets fixed in a patch. My instant of this bug sorted itself out in a few days.
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Fallout: New Vegas - Caravan Basics
T he aim of the game is simple. As stated, you need to get your three tracks between 21 and 26. The winner is the person with the two higher tracks once the third is completed (both are in range and a winner exists).
Each game starts by laying out a foundation. You will want your foundation cards for the three tracks to be low or high. Do not use middle cards like fives and sixes unless you plan to use some fancy tricks to reverse the direction later.
Direction is really at the heart of the issue. Caravans have to be loaded in one direction. If you start with a three and play a two, you can only play an ace (unless you have a suited card, which we'll cover in a second). The reverse is also true. If you play an eight on the three, you can only play a nine or a ten on the next turn.
The exception is if you have a card of the same suit. You can ignore the direction of the caravan if the card is of the same suit as the one at the bottom. Note that this also reverse the direction of the caravan. This is useful if you find yourself backed into a corner and need to open up a few more options.
The heart of the game is still pretty simple. Either match the suits or continue the chain with your numbered cards until you get to 26.
It gets really interested when you include face cards.
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Fallout: New Vegas - Caravan Basics - Face Cards
J acks are easy. If you put them on top of a card, this will remove the card and remove any face cards that were put on top of it. This is very useful if an opponent uses a king to build a track quickly at the start of the game.
Queens are useful in certain situations. Playing it on a track will reverse the direction of the track, as if you played a suited card. Queens have no value, but it can be useful if you are forced to start a game with a weak foundation. I've had a lot of luck building a descending caravan with low cards to reach the teens, then using a Queen and a ten to hit 26 and secure that track.
Kings are also easy, although they have a few uses. Kings will double the value of any card that they are played on. If you use a king on a ten, then you can probably wrap up a caravan in a few turns. Kings are also good near the end of the game when you're trying to work a 24 or a 25 into a 26. Playing a king on an ace can edge out your opponent. More interestingly, you can also play Kings on your opponent's tracks to overload them. If he has a Jack handy, then all you did was make him waste his Jack, but if he doesn't it can force him to abandon an entire track to you.
Jokers are interesting and really wild. A Joker played on a numbered card will remove all other instances of that card in the game. Note that this includes your own tracks too, except it will ignore the track that it is played on. If a Joker is played on an Ace, it will remove all instances of the Ace's suit from the game, except for the track that it is played on. I personally don't use Jokers much, since they tend to do a lot of collateral damage to your own tracks. They are useful as a last minute desparation move though, if your opponent is just overwhelming you and you need a reset.
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Fallout: New Vegas - Caravan Tips
Caravan is mainly about getting the basics right. If you can stack your numbered cards up right and use your Face Cards to bust or harass an opponent, then you will probably win the majority of your games.
Note that there are a few more things that you can do by building your deck. When you enter the game, you are presented with an option of looking at two decks. The top deck is your active deck that you're going to use in the next game and the bottom one is the entire deck. Cards visible on the bottom are not in play. You can add and remove cards as you wish.
The general idea is that everything is a tradeoff. If you use less cards, you will be more sure of what you get, but you run the risk of running out of cards and limit your strategy.
With a little practice, you can probably prune your deck though. I usually don't use many Queens or Jokers because I don't find them to be useful in my games. If I'm going to have face cards come up, I want them to be Kings or Jacks.
Another strategy is to limit yourself to only two suits for numbered cards to give yourself greater mobility in your game. Personally, I think that that's a little too much work for no real reward, but it's an option for anyone that's having trouble with a tough opponent.
As to who you should play, there are plenty of potential opponents, but a few really stand out. Travelling merchants, general merchants and adventurers usually know how to play. In particular, the NCR Ambassador in New Vegas, Dennis Crocker, seems to be the highest better I've found. He'll happily go up to about one thousand caps on a single game. For easier access, you can talk to Lacey in the Mojave Outpost Bar. She usually bets about 600 caps. No-Bark in Novac is usually willing to bet a similar amount.
Hopefully these basic Caravan tips will help you get some easy money in Fallout: New Vegas and let you have a little extra fun in the game.