What I might do is require one skill challenge for their entire bulk of gems. I'll also try eriktheguy's idea and have different cultures favor different gems.
See, I don't want gems to be functionally identical to gold pieces.
The best I've got so far was giving each nation a different currency, so the players need to hold on to their gems (or melt down their gold pieces) when they travel to different countries. I would like to impose some sort of mechanical difference as well.
I head Accountants & Attorneys the RPG has whole chapters devoted to this...
Seriously, I wouldn't bother. Gems are basically currency, and can be spent like money in places where you by things that are on their cost scale, like a big city. If you come to a poor little thorp, they would probably stare in awe at a gold piece, perhaps even a silver piece, and quite likely not understand what a gem was. But then again, you could bye the whole thorp and everything in it for the value of a gem, so there is nothing there yo trade it for anyway.
Get hold of the Anime series "Spice and Wolf" (Spice and Wolf - Wikipedia, the free encyclopedia), using any means at your disposal!
See, I don't want gems to be functionally identical to gold pieces.
So to summarize this thread (from my point of view)
- gems work like currency by RAW, but are lighter,universal currency, better for gifts/bribes
- requiring skill checks to sell gems is a no-no
- optionally allowing skill checks to sell gems is tedious and could be abused
- specific, valuable gems might be worth a lot to particular NPCs, and can create encounters and adventure hooks