So I need to make a bunch but seems like the easiest way to get them to look perfect is by using a mould or silicon cupcake pan..none of which I could find locally.  

But I do have a cupcake caddy, where the top portion is shallow and looks perfect for the dip.  Question is its plastic...so what can I add to make it non-stick when I pour the candy melt?  They need to pop off to look perfect...

Im think greasing it with crisco? And adding a circle parchment paper ad the bottom so atleast I dont have to worry about the front?  Any other ways to get them to look like this...

Unless you need them done ASAP, I would definitely order a mold online if you can't find it locally. It would save you the headache. And its always good to keep a few molds on hand for big orders. Fill with chocolate, then cookie, and cover with chocolate, pop them in the fridge and they're ready to pop out a few mins later. You can find them on Amazon, http://www.amazon.com/dp/B007N75XEG/?tag=cakecentral-20+oreo+mold

Thanks unfortunately Im in Canada and havent seen them at the usually places that carries baking stuff. 

AWhile I was in pastry school we dipped candys in chocolate and used a tool similar to a fork with only two prongs. Drip in a deep bowl of melted chocolate, Slide the fork underneath it, let chocolate drip, and then slide off onto parchment, put in fridge to get solid. I can't remember what the tool was called but that is the concept. Hope that helps some.

AI normal fork may work just as easily..