So I week passes and I decide to try it again, this time using paintable acrylic caulk. It actually went pretty smoothly the second time. The only problem I ran into is using caulk to create ridges and such means it goes on fairly thick in places, and it takes a long time to dry completely through. I had it done and painted 2 days before the game, and while it was certainly dry to the touch, it was still a bit mushy in places when you placed a heavy object on any of the ridges. Rolling it up to take it to the game ended up putting a few cracks in the caulk (nothing I can't fix later with a bit of paint), but if I were to do it again, I would want at least a week or two to let it dry before using it. Anyway, here are a few photos. One of it plain, and then several in use.
Hope you enjoy.
The last picture is of my first attempt. You can see where my daughter walked across it and took the paint off.
Sorry for the ok quality photos. Since upgrading to iOS 8 on my iPhone it's been taking really crappy pictures.