I'm just at the point where I feel the randomization of it has become worse than the problem it was designed to fix.
I can see that. That's why I favor a subjective system. Let front offices vote to determine the order of the picks. You can pretty much guarantee that the "wisdom of the crowd" would get the best pick to the worst teams. At the same time, teams that "tank" (something that everybody subjectively says they can put a finger on but nobody has ever objectively identified) could still have that taken into account.