I think James has picked the right target for his catalog values. I disagree with a few of the values, but there are LOTS of different chips in the catalog and he and I won't always see the same chips for sale.
Remember also that a chip show is a market... you should expect to shop around and negotiate with dealers who have items you want. Buyers who only pay the price marked will generally end up on average paying more for their collectibles.
Finally, one thing I have learned about the hobby and collectible shows in general is that dealers will give you a better price if you buy several items at once. A discount is almost always offered if you buy, say 10 items, or maybe a couple of hundred dollars worth. The discount comes off the marked price. James catalog value generally represents what you can see marked on the item, not necessarily what you actually pay after doing a deal.
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