Good of you for buddying up and being geared properly.
Have you considered
https://boardandkayak.com/article/kayak-outriggers-1669763630653
Young summer camp me could do eskimo rolls all day long even without a paddle.
Old me promptly toppled over several times, and could barely squeeze into the thing despite sub 1" layer over the greater trochanter.
You definitely didn't skip shoulder day
