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My suggestion, take it or leave it:

1. Look at the guns currently in your inventory and find the ones you are most proficient with, are reliable and are concealable/reasonably comfortable to handle (no sharp edges/corners).

2. Read as much as you can in the holster-related sections and threads on this forum and take good notes.

3. Get the best holsters you can buy for the guns you have.

Holsters are a lot cheaper and easier to trade than guns. Make sure you take a look at the dead holster drawer here (or whatever it is called).

All that said, quantity does have a quality all its own.