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Interesting. As a datapoint, I was unexpectedly gifted Airpod Pros for Christmas and all three tip sizes seal well in my ears according to the test app. The middle sized one is most comfortable. Regular Airpods fit fine.

That being said I'm planning on passing them on to somebody without Airpods (after buying new eartips!) because I already own regular Airpods and Bose QC35s. I prefer the on-ear Boses for ANC and the Airpods for comfort (not completely in-ear, easy to take in/out for casual listening, less isolation than Pro's transparency mode, they fall out and pause playback when I fall asleep).

The Airpod Pros aren't bad, they would be a good compromise between the two for somebody who likes in-ear buds. I just don't have a use for them and find them overpriced.