Use a circle cutter for the petals, and do it pretty much like a fondant/gumpaste rose... only use gloves because the chocolate will let your fingerprints show. There is a type of glove that I've seen others talk about to use when working with chocolate, but I don't remember what it is right off-hand. HTH!
If you have other, more specific questions, feel free to ask, and i'll help as best I can. I've only made these once before, but found it's like using the other mediums. 
I am wondering if anyone knows how to make rose cake pops with modeling chocolate. Any advice would be greatly appreciated : )
When I make my rose or rosebud cake pops, I use an egg or oval shape cookie cutter. I bake my cake pops instead of mixing the cake and frosting method. After baking and cooling my cake pops, I dip my lollipop sticks in either melted candy melts or white chocolate chips, then I stick the lollipop stick in the rounded bottom part. My cake pops sometimes have pointy tops, this works great for making this. Next, chill them to have the the cake pops glued to the lollipop stick. Dip the entire cake pop in the melted candy melts/white chocolate and again, chill them or let them air dry. I prefer chilling. I have experimented with melted can frosting this winter - cream cheese, boy was that good. Once they have been dipped, I put them in the fridge to chill 30 minutes or over night. Finally, Use modeling chocolate in place of fondant. Cut about 5 to 6 oval or egg shaped petals. Take the 1st petal and cut in half. Form a pointy loop and glue it on top of the cake pop with piping gel. Then add petals one by one until the whole cake pop is covered. HTH
http://cakecentral.com/gallery/2256431/more-flower-cake-pops
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