Are Roshi and Korin referring to Prime Roshi? Or Post Korin Roshi? Is Prime Roshi > Post Korin Roshi?
Did Roshi really say might in the word for word JP manga tho? He may very well have used that type of uncertain expression, I agree, but I've seen some sentences Herms had translated, like ones expressing uncertainty of some sorts such as "likely"... that when I was double checking the JP raw scans, "likely" wasn't the best word to describe the comment which expressed stronger assuredness — iirc it was old Kaioshin saying base Goku/Gohan Potara would [likely] be plenty vs Boo"... The word was closer to "definitely" iirc.
It's still a little bit different though because Roshi had a clear urgency in defeating Goku, so much so he used unorthodox moves like the hypnosis jus to win.... If Kuririn had recently fight Tao Pai Pai and Kuririn or Yamcha had the slight advantage, then I think it'd be more comparable to the one you were referencing... Like, when we weigh on how much can a comment/comments be fair reasoned to change the scaling, or just be too contestable... Like Freeza implying Goku was the first one to surpass Ginyu is a bs statement that is just totally ignored.