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Cardboard of the Rings 
Turns out you’re all wrong.
Quote from here: https://community.fantasyflightgames.com/topic/225784-prince-imrahil-the-flame-of-the-west-ally-and-caldara/?p=2325945
Prince Imrahil is an ally with the conditional passive text: While there is a hero card in your discard pile, Prince Imrahil loses the ally card type and gains the hero card type.
Caldara has the action ability: Discard Caldara to put 1 spirit ally from your discard pile into play for each other hero you control with a printed spirit resource icon.
I went ahead and asked Caleb how these two interact with the scenario that my 3 starting heroes have the printed spirit icon, one is Caldara, the Prince Imrahil ally is in play and is still an ally. Then, I trigger Caldara’s ability. How many allies do I get out of the discard pile? And here is his response:
Hi Benjamin,
Prince Imrahil’s text is a passive effect that is constantly checking the game state to see if there is a hero in your discard pile, so the instant that Caldara is placed in your discard pile he becomes a hero. As for Caldara, the cost to trigger her effect is to place her in the discard pile, and you cannot trigger an effect without paying the cost first. So, you must discard Caldara before you can resolve the rest of her effect. That means Imrahil is a hero at the time that you calculate how many allies you put into play, which means you can get up to 3 allies into play with Caldara’s effect (or even 4 if you make a unique spirit ally a hero with Sword-thain first).
Cheers,
Caleb
Dang. Nice clarification!
And I agree with the GenCon assessments: don’t overbook! I already have for this year, but not as bad as last time.