I guess in this digital age it is harder for players to just "disappear", and more and more guys seem to do private signings now and remove themselves from this list. Any player still living could suddenly become quite attainable for a price, and once set collectors are satiated the market all but disappears. Examples that come to mind are John Christensen, Al Pulido and Jim Traber.
A few guys in the popular 1987 Topps set can be very pricey on that specific card, but cheap to downright common on other issues. Players like Tony Bernazard, Mike Brown (the Seattle pitcher), Rod Scurry (also insanely tough on 89 UD) and Frank Wills come to mind in that regard.
That said, a couple toughies that have yet to be mentioned in this thread are former Mets infielder Kelvin Chapman and Astros pitcher Mark Lemongello, even though the latter recently did a fairly expensive private signing. His story is definitely worth looking up if you are unfamiliar.
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