I usually have at least one for each type gun that might see use.
Using guns of the same make can also save you quite a bit, as very often, the same holsters can be used for different guns.
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If you play with handguns long enough, you'll have a couple of boxes of holsters too.
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If you want to recover some of that money, EBay is a great place to do it. I had a couple of boxes of old holsters, and made out very well selling them there.
Its also a great place to buy good holsters for very reasonable prices.