I'm sure the YouTuber Dogen's name would not be strange to a lot of people here on this site, and I'm sure a lot of you have seen his this video where he makes fun of words that sounds similar.
Specifically, if you watch the first minute of the video, you can see he makes a skit from the word 決行{けっこう} and 欠航{けっこう}, which mean completely opposite things in that context of a ferry ride.
My question is: is what he's showing a possible real-life situation? If not, why? Can people ever mishear 結構{けっこう} and 決行{けっこう} and 欠航{けっこう} since they could all make sense in the same context?
P.S. I know the pitch accent is slightly different but is that the only distinction between these words when spoken? Do you have to like draw kanji in the air to convey the right word sometimes?