Hi Hayden

I share your frustration at values for chips I've purchased going down, imperfect knowledge of the "true" number of chips available and the like.
That some chips (read: coins, stamps, old dollar bills...) will not return what you paid for them is an unfortunate part of the hobby (investment).
Any Investment (hobby) will only give a return based on the knowledge and skill you acquire in it's pursuit.

I travel in the cheap end of the market, and personally, I never pay more than a few dollars for a chip. So my downside (per chip) is very limited. In the process, I gather knowledge and resources and hone my skills, so that when a real deal comes my way, I'll know it. Some of that knowledge is that boxes of chips ARE still being found, and that semi-rare chip that I paid 20 bucks for is now readily available for 3 dollars, so I "invest" accordingly.

Are the ones that you are buying pretty to look at? Do you appreciate the artwork, or history, or manufacturing process. Is it the primal thrill of the hunt, even if it's just waiting for one to show up on eBay for 50% less than it normally sells for? Do you enjoy discourse with friends about your latest find? If it is worth 20% less today than when you bought it last year, did you get value for money in some form of enjoyment?
How much intrinsic value is left from the movie you went to see last week?

I buy a lot of current, new release, dollar chips at 3 and 4 dollars each. I know for a certainty that there are boxes and boxes of them walking out the casino door. Will they ever be worth more than a Dollar? Will they ever sell on eBay for more than 3 dollars? Not betting the farm on that one. Am I being ripped off by the seller not overtly stating that he has hundreds of that chip in inventory, and charging me several times what he paid for it? I'd say no. It'd cost me more than the few extra dollars charged, in gas money just to drive down to the strip and get one for myself. If someone finds a box of chips, who should profit most from the find? The guy who did all the work to hunt it down, or the guy who wants one as cheap as possible for his collection?

Chip Collecting is still a Gentleman's (and Ladies') Hobby. If you've ever been a coin collector, you know about slabs; marketing, and population reports. Slabbed coins trade sight unseen, as a commodity (investment?), based on some Grader's (a person you've likely never met) opinion of the coin. Where's the fun of that? You can't even get the coin in your grubby little paws, while it's in it's plastic tomb. You never have to learn how to judge and appreciate the difference between grades, just look at the number on the holder and you're done. Oh, there is still some enjoyment in tracking down the various coins you need for your collection, but the level of skill and accomplishment has dissipated. Chipping is still a matter of getting the beast in your hand (at least getting a good scan on eBay, ugh...) and discussing the condition and price with the seller. The enjoyment is trading knowledge, doing a bit of relaxing research, gaining knowledge for knowledge's sake, and appreciating the beauty you find in the objects of the hobby.

Yes, there are some less than gentlemanly folks out there selling chips, Real Estate, health insurance... Welcome to the modern world. Just don't let the [children of unmarried parents] wear you down :-)