I had played two Aristocrats earlier in the turn that were still in play. I played Specialist and used it to play Aristocrat. I got nothing and nothing. Is this an error or am I interpreting incorrectly? I expected Specialist/Aristocrat play to result in +$3 because a third Aristocrat was in play, and then replaying the Aristocrat, resulting in +$3 again because an additional Aristocrat was not added to being in play. Instead, neither play got me anything.
Your interpretation is correct. You should have gotten +$3 twice in the situation you described.
I looked for the game but it doesn't load (internal error), so I guess something did go wrong in that game.