Not sure what people are expecting when signing castoffs.
Sometimes, teams make bad personnel decisions. Instead of journeyman who have bounced around several NBA teams or veterans well into their decline, I'm more interested in guys who never got a fair chance to show what they have in the NBA, either because they never caught on in with a team or because they never got enough playing time for a poorly-run team. That may sound counter-intuitive, but guys who couldn't get playing time with bad teams should be looked at more closely because they are more likely to have been misused or under-utlized than players who couldn't get playing time on well-run teams.
There is a reason why finding a gem in the rough rarely happens like this -- there are 30 GMs doing due diligence in the league. Sure, you can slip by a handful of them because they're duds, but if you can play in the NBA, you eventually end up somewhere.
I'd argue that it happens less often than it should. Teams tend to over-value veterans and known quantities relative to players with little or no NBA experience who are more unknown quantities. GMS often seem to have emotional ties to players they drafted and are unwilling to admit a mistake by cutting such a player in favor of someone who may have gone undrafted.
By understanding the biases of NBA front offices, you can come up with a profile of players who will be undervalued by teams. If many teams are squeamish about under-sized players, you might find value by getting shorter players who are more productive than guys who have a couple of inches on them. Right now, it is obvious that the D-League will always have at least a few guys who can step in and contribute right away in the NBA, although it is not obvious who those guys are. It is just as obvious that some teams are overly skeptical of the D-League and don't see it as a resource.