Prepare yourself for some reading here.
The transfer sheet adhered completely to the chocolates, coming off cleanly when I removed it to pop the chocolates out of the mold. But the parts of the transfer sheets that were touching the chocolates had broken apart. As far as the temp of the chocolate itself...I'm not sure what it was. I didn't use a thermometer to check. A dumb oversight on my part. The only thermometer I own was being used for the caramel cooking away, at the same time, on the stove. I now know this to be flawed logic on my part as I thought the caramel would be far more temp-eramental than the chocolate.
I tempered the chocolate using a Wilton Chocolate Pro. I melted some of the chocolate first on the "melt" setting. Then turned the setting down to the "warm" setting and added more room temperature chocolate to bring the overall temp down. Once all of the chocolate was completely incorporated/melted, I proceeded to pour it into the molds, drain and scrape off the excess, and pop it into the fridge to cool. I do know the caramel was hotter than the chocolate when I divided it into the molds. However it did not melt through the chocolate coating the mold walls. The caramel was completely and beautifully encased in chocolate when I popped out the finished product. None of it had leaked/seeped through to the outside of the chocolate.
In writing all of this, it has dawned on me like one of those "well DUH" type of moments, that my chocolate was probably too hot when I initially poured it into the molds from the start. The problem with the transfer sheets breaking apart was probably exacerbated when I was tipping the molds to drain and scrape the excess off. Then further exacerbated by the expanding and contracting that probably happened when I put the caramel in.
So in winding this post down I am pretty sure I need to have the chocolate at a cooler temp before I go pouring it into the molds to start with. That extends to having the caramel at a cooler temp when it goes in as well. Which leads me to my (hopefully) final question: what temp should the chocolate be when I go to pour it into the molds? I am ordering another digital thermometer as soon as I'm done typing this. As not having one for both cavity-inducing, sugar laden goodies (the chocolate and the caramel) will not be another future oversight on my part.