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There are three shopkeepers - one in Dodge, one in Empire, and an Indian Trader. Each shopkeeper is a separate store with his own unique items.
The shopkeepers work in a very strange fashion. Each shop will only ever have a total of 10 items. They show you 5 to start with. If you buy one of those 5, you get to see the "second item for that slot". If you buy the second item, then nothing else ever goes into that spot. It doesn't matter how often you come back.
Note that you can EASILY buy every single thing if you do the extra missions, so don't stress about buying everything immediately. Just buy what you need the most and get the other things as you go.
The things you buy show up in your saddlebag. It only shows the "best" of an item in a given slot. If you buy a basic speed loader and then an advanced one, the advanced one takes over the spot the basic one was in.
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