Maybe this should be split into two competitions: one for designs that apply across an entire set of chips, and one for a single denominational inlay from a set featuring significantly different inlays?
The first category could include sets like the Dunes, or Treasures, whose denoms all differ only slightly, e.g. by color, or printed denomination.
The second would evaluate single extremely strong inlay designs from sets whose other chips or denoms might be significantly weaker. An example (for me) is the Mesquite Star large star $25, which is without a doubt my favorite $25 ever -- but I wouldn't take the small star lower denoms as gifts.
Just a suggestion -- it'll be fun either way.
Could be interesting, but I think there are too few sets with all unique chips that would fall into the latter category, so probably a better idea to just throw them all into the mix here.
Plus, I kind of think of the ability to keep the quality consistent over multiple different chips in a set as part of the strength of the full inlay design of the set. In that way, a single design can include several different iterations (as mentioned in the OP, the PNYs, for instance). It can be kind of a high variance design strategy depending both on the ability to come up with good designs for all chips and also on whether people like the multiple-chip design. When executed well and people love them, huge win. If executed poorly or people don't like the idea, the overall design will rate more poorly.
I'm still thinking about this and I'd be open to suggestions (from Larry or anyone else) as to how to handle sets with multiple designs across denominations. My initial statement in the OP was that I would post only a single chip in the voting threads, but maybe that's not the best course.
To take an example in which I have an interest given my nomination, the Caesars Atlantic City set is only such a good design imo because of the multiple designs. I'm sure many feel the same about the PNY inlay(s). Seems like a slight to the sets that fall in this category to present just a single chip. But I also wouldn't want to set it up unfairly to those sets with only one design. People would be looking at nine different Ritz chips versus one single Kings Castle chip.
For the moment I'll stick with my original plan and just leave the job of posting different chips from the set to people advocating for the set in the thread, but I'm not wedded to this as a rule.