it looks like a medium 5 petal flower cutter...I would not let them "dry" I would let them get a bit firm then start adding them to the top tier. when I do a ruffled tier and want the fondant to ruffle a certain way, sometimes I'll place a balled up piece of wax paper or paper towel in there until it sets. I don't think it will be too difficult to achieve the look you want once you start placing the flower on it. Good luck!!!
Yeah, you don't want to let them dry, those should be put on the cake while they're still flexible. Just cut them out, shape them a little (thin the petals or put them in a veiner or colro them or whatever you're going to do) then press them onto the cake with a ball tool and keep doing it so that they all fit together and cover the surface. It's very easy but time-consuming.
This tutorial might give you an idea on the ruffles only you would have to attach down side up.
You can just start at the top and do the ruffles. But she does those "ruffles" more like a strip of fondant that's rolled really thin then ripped up at the top edge, and she turns the cake upside down to attach them. Totally unnecessary, really, you can just start at the top and work your way down to attach them. Just do them really close together and rip the top edge instead of making it really ruffly. I did this blog post showing how to do ruffles from the top down, so just make the strips less ruffly and more torn-up looking. I can't do them torn-looking like that, it drives me nuts to make it so messy, but this will give you the general idea. http://acaketorememberva.blogspot.com/2011/11/ruffle-wedding-cake-tutorial.html
Thank you everyone! I have a few weeks to grasp the entire ruffle concept but I appreciate all the links and helpful tips!!! :)