I loaded up a case with a bunch of gems, about a 100, it looked so cool. Then I left the house, remembered I needed something, came back, and all my gems were on top of the display case. And, of course in trying to pick them up, I triggered the case lid to open which scattered the jewels all over the house. I just reloaded to before I even put the jewels in.
I don't use the display cases anymore.
I did not drop them on the ground first, not doing that with 100 gems.
I tried a few gems in display cases, not a lot of them. One of those wooden trays is best for gems, like the one on the floor in the entryway near the main hall door. You can try them in a small bowl sitting on something, but defying the laws of gravity the bowl will tip over as you put them in unless you are careful. One of the more flat bottomed silver bowls is best to try out for that. in Oblivion we could just put them on a plate, but in Skyrim they will escape and go everywhere but the plate when you return.
I put my gems in the display case (and in just about everything else) by directly dropping them where I want them. I will just line it up and pick up the mistakes till I get it right. They always stick.