We transport our cookies in pizza boxes. That would solve your delivery problem. Then you wouldn't need to worry about hurting them or piling them on top of each other, and could decorate them in buttercream, which is what we do most of with our cookies at the bakery I work in including our shipouts, which have gone to IRaq and Korea and come through just fine.
You would have to cut yours out by hand after making a template. 2 dozen isn't too bad. But to do all the stuff, with the cutting of the fondant and all, you would have to charge a whopping price just for the labor alone. If you aren't an artist and couldn't draw the details on the cutout by hand you have a big problem. Then you will have to do an edible image. We have used hand made templates for certain cookies we don't have cutters for. You can use heavy duty cardboard or get one of the kids in the high school shop class to cut you one out of thin plywood.
Sometimes, you just have to tell the folks who have been watching the cake shows on the food network that their idea isn't feasible for what they want you to do. Nor would it work with their budget.
Hope this helps. Good Luck.
Red from iowa