Ok, so here's the update I finally promised:

First, I found a crazy deal on the laminating pouches I needed, so I nabbed 1,000 of them. No sense in running out during the experiments! :-)

Above are the prototypes (pre-abuse) made with clad dimes.
After lots and lots and lots of testing, I found out that thicker is not necessarily better. The thicker cardstock (even plastic coated or otherwise 'ruggedized') where it "felt" more substantial, tended to separate when laminated and flexed and bent enough. Thinner paper did the job to keep things flexible, durable, and all in one piece. I also found that thinner paper worked better where the bulk of the card was a hindrance to sticking more than two of these in your wallet.
I calculated out the perfect size ratio to get a nice "blister" bubble around the coin. This way it is hermetically sealed and isn't going anywhere, even if the card is significantly damaged. It's a *real* trick to get the coin out with only your hands as it's tough.
As you can see in the examples on the left-hand side where the collar was too small, there was some unsightly discoloration of the plastic where it couldn't seal to itself (it became cloudy). Also with these, if flexed enough, the paper would give way and separate, regardless of its thickness, making the coin loose and prone to move around in the packaging. The completely-sealed blister was the best choice. :-)
Once I got the overall ratios down, I fiddled with printing. I worked out all of the kinks of duplexing as well with printing blanks and running the blanks through a second time for serial numbers. I also can alter the serial number template so I can outsource the actual printing of the blanks to a local print shop if need be; however, my current setup is more than sufficient for the current scope of my experiment.
I then had to go about cutting them out. Luckily, I have a CraftRobo Pro CNC paper cutter/plotter which did the job perfectly. All of the outlines were programmed in and each paper insert is completely uniform in size with smooth edges. Peeling them off the carrier sheet and stacking them up was quite satisfying. :-)

Finally, I assembled the first 26 examples (as they're printed in multiples of 8) and here they are, sequential serial numbers and everything.
All I need to do is finish working on the software end of things (value tracking, etc.), photograph them, and they're ready to be released into the wild. :-)
If it's a 'success' (and I'll call it a 'success' if I'm able to find at least 3 local stores that will accept them at Trade Value, which is over spot) I'll see about offering these somewhere for everyone who has expressed interest.
More pics (and perhaps video of the cutter at work) later!