Having worked at Imagineering under both Iger and Chapek, you'd be surprised at what decisions flow to that level. I think the major difference is that Chapek was *only* interested in cuts and savings; you simply did not bring him anything that would cost more money for a better guest experience because he didn't want to hear it (and, in fact, they wouldn't make it to his level because lower-level execs would just remove anything like that before it got to him). Under Iger, and particularly the "new" Iger who has made it pretty clear he thinks we need to recover from the brand damage done under Chapek, I could see Josh D'Amaro bringing something for Iger's approval with a long list of amenities, enhancements, and improvements with a price tag at the end--"Boss, if we want to live up to our brand promise to our guests, I'm going to need $120M (or whatever) this fiscal year to implement my "Project Sparkle" initiative." Iger might approve it on the spot, or he might say something like "You can have $80M, so you figure out what fits in that budget."
So no, Iger probably wouldn't go line item by line item and judge whether it's worth $1M a year (or whatever) for Aulani to hand out flower leis and provide cool drinking water at check-in. But I could definitely see it being part of a presentation to him.