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To me, it's not a problem with "spicy & sweet". It's more a problem with "meat & frosting/icing/glaze". Or "beans & frosting/icing/glaze" if it's veggie chili.
An un-iced cinnamon roll would be unusual to my palate, but probably taste fine dipped in chili. Similar with sweet cornbread, brioche, sweet "school" yeast rolls, etc. Cinnamon-raisin toast would probably be fine with chili, as well.
But, say, a glazed donut? Birthday cake? A Ding Dong?
I'm from Cheyenne and cinnamon rolls with chili was absolutely a staple growing up. It was the only good food they had for school lunches - no one brought bagged lunch on chili day.
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