There are lots of considerations in pricing cancelled chips. If there are next to no chips available uncancelled, there will always be a market for the drilled chip. If there are lots of the drilled chips, there's a market, but it will be at a huge discount to the value of the regular chip. If both cancelled and uncancelled are readily available (like some of the Aladdin chips) and there will only be maybe a 20-40% discount for the drill hole.

Part of the demand for cancelled chips is to fill a space in your collection until you find one uncancelled. I've done this many times, and often it will take years to find one uncancelled. Meanwhile, you have a chip to look at in your collection. TCR is starting to put values for the cancelled chip in addition to the uncan. I think this is good, and will help answer questions like yours. There are chips like some of the Harolds Club portrait series where only one or two are known without the hole. Some collectors ignore these, afraid that someone has a box of the uncancelled chips. The risk is somewhat dependent on how long the hobby has gone without an uncancelled chip being discovered.

A consideration, although not a big one, is that it's possible to fill a drill hole in a cancelled chip. There are "chip preservation" services that will do this and it's almost impossible to see the repair. You won't likely see this on common chips as it is a time consuming process and will likely cost you quite a bit. Although I've not had this done myself, I would put a significant purchase premium on the repaired chip over the raw drilled one.

I've also seen and owned a few chips that were casually filled by a previous owner. The repair is obvious and didn't cost him much. I wouldn't value one filled this way much over that of a drilled chip, but they do look a little better in your collection.