I have never had a single Outpost $100 chip. Missed out when they were "cheap" and did not get around to picking them up for the set. (I also didn't buy the rack of $0.10 chips either at $700/rack. But I was tempted.)
Don't put a lot of credit on the market values for Outposts - the market is set by six+ month old auctions representing only a few racks. That being said:
$0.25 go for ~$2/chip. The spots are mostly split, the condition is lightly used and there will be spinners.
$0.50 might go for $1/chip. Grand inlay with a few old style chips. I do not recall ever seeing the old style in rack quantities.
$1 chips are the biggest part of the Outpost family. They are USED, one of the most worn chips you might see. My players love them for the butter smooth surfaces. ~$0.50 per chip
$2 chips are uncommon, maybe go for $2+/chip if anyone is selling. Almost new, there will be spinners.
$5 chips are second only to the $1s - very common. Not as worn as the $1's but nothing close to uncirculated. You might find a near mint rack for top dollar, but the used ones are worth $0.75/chip.
$20 chips are the third workhorse chip from Outpost. Better condition than the $5s but still casino used. There are a few uncirculated racks out there but the used ones are ~$1/chip
$25 chips are uncommon and uncirculated to very good condition. $2/chip?
$100 chips are less common and likely would sell for more than $2/chip, but who knows?
Back in the day, you could buy 1,000 outpost chips for $600 (600 $1s, 300 $5s, 100 $20s) The original seller would sell other stuff. Rarely you could get good deals, unlike today where the seller expects single chip pricing for racks. Outpost has two locations with different chips. They also replaced their chips with grand inlays at the very end of their run.
I have something like 2,400 Outpost chips, notably 400 $0.25 chips and 100 $2 chips. My playing set is 200x $0.25, 300 $1, 300 $5, 60 $25 and 100 $100 chips from river city.
DrStrange