I've attached some images of the size label that The Original Poker Chip Customizer does. As you can see, on the dice chips that have roughly 15/16" center, they look great and fit perfectly. For the other chips, it's really up to taste. You can see that there is a lot more space between the label and the outside of the chip, and for the blank chips and chips that have an image smaller in the center it will work well. Not sure of the pre-printed chips though with a larger image in the back, still up to you there.
As for the software. I designed the software to be user friendly and included a well documented instruction manual to step you through creating a chip with one of the out of the box templates, or importing a picture to use on the chip. Both instructions are very easy to walk through and I haven't had anyone complain yet that the system was too hard to use.
Thanks for your message.
...Dan
(sales@chipcustomizer.com)
(http://www.chipcustomizer.com)