In regards to 2 or more icons...
Sweet 16 in 2006 literally used Jack, Caretaker, Director & Storyteller for the event's 16th anniversary. All four appeared in marketing. It wasn't crazy. But they only got away with it because of the anniversary. Each icon was also attached to a house (2 of their own sequels, 2 in unrelated sequels).
They didn't attempt this again with the 20th, 25th, or 30th. If they did want to try, I'd rather see the icons that came afterwards- Bloody Mary (if only
), Usher, FEAR (he deserves a 2nd chance), Lady Luck, Chance (the other 2nd ....chance
).
Fun Fact: The concept of TWO icons is nothing new. Back in the golden era of icons, with the old creative team for HHN, they DID dream up ideas of a two icon event. Of course, this was also back during the ambitious two-park event concept. One icon would be for Studios, the other for IOA. Off the top of my head, one icon duo was "Jack & Jill" (would later become Chance in 2007). I'm too lazy to elaborate further, but just wanted to point out the two icon idea isn't "new".
/End history lesson. Class dismissed.