I hope you are typical. Personally, I find it shocking that many of the same people I've seen balk in the past at paying even $50 for nice vintage items have no problem dropping hundreds on Old School boxes. As much as I dig this series, without caring about the sketches, it makes no sense for me to pay for boxes I can get for next to nothing, even while STILL being able to rip packs.
Let me compare it to something you're familiar with, Jason, though the comparison is far from exact. In the comics industry, in the early '90's, changes were made to the nature of the comic book product in order to attract a certain segment of the consumer dollar. Many of these changes alienated the long-term customer (me), and once the short-term customer moved on the bottom did indeed fall out.
Admittedly, this is not really comparable, because having sketch cards really doesn't directly alienate anyone who doesn't care about them. Chase cards in general do alienate some collectors by foiling their completist tendencies. And it could potentially alienate customers if they are later required to pay full price for boxes they've come to expect to get for pennies. I do think it's a bit dangerous when three to five people are buying a significant percentage of a print run, because it makes things unpredictable going forward.
I think the key, with regard to Old School, to avoiding the problems you point out, is to keep to their original and I feel, well-thought-out, structure. Key among that, is the print run, and the price point - and the quality of the main set. If this were a mass-market thing, I think it would be more susceptible to the legitimate issues you point out - because we have already seen that happen.
I don't want to answer back with things you clearly already understand, but as you know, the harm in comics came about from more than just special covers, but they were certainly part of the problem. But again, I think we all agree that the comic and trading card businesses made a lot of mistakes, at least in retrospect. (And I've not doubt we could discuss all of that in detail for many hours - I certainly could.)
The fact is, trading cards and comic books, such as they are now, are not the same kind of consumer product they once were. I realize that some folks may take issue with that, and I invite the discussion, but I would have a tough time being convinced that they are what they used to be, to the market they used to serve. Pricing and chase cards, and changing tastes in entertainment have all contributed to that. Trading cards and stickers are not a significant part of youth culture, as they were 40 years ago. They are something different now. But I feel that Old School is doing a terrific job balancing the various sides of it - it's a series that is true to some much of what we loved back then, but it acknowledges that it is being sold in 2011.
My conclusion is that, as long as the quality of art (in the core series) remains high, and the print runs remain limited as they have been, and the price-per-box doesn't see any inflation, this series has a bright future ahead it, whether the interest in sketch cards sinks or soars to new heights.