How to create a stamp that randomly places images?

[chaosb29625462]

Hi! I'm pretty new to Photoshop and I've been having trouble with stamps. I remember hearing that stamps can be custom made from a single image to be easily placed in a pattern with easy-to-manipulate parameters (ie: space between stamps, orientation, etc...), but I was wondering if I can throw a couple images in the ol' stamp machine and use it as a tool to procedurally generate a bunch of them. In this case, I have 7 tree PNGs that I would like to place randomly in a portion of my background image, but it feels like doing it by hand would not be the most efficient way of going about it.
I'm using this project to acquire best practices, so even if taking this "shortcut" extends the original timeline, I don't really mind. I'm excited to hear your solutions, thanks!

[Chuck Uebele]

You can create a pattern, which can be multiple colors, then use one of the Deco Fill scripts to fill an area