I also do agree with you now that Kuririn was probably referring to a hypothetical Full Power Roshi when he said Jackie Chun was overwhelmingly superior, the same way Kami-sama was referring to Piccolo Junior's reserves after saying he was severely outclassed. So maybe Roshi showed Kuririn's estimations for his full power when finishing off the bald guy?
The Oozaru hadn't been introduced via a multiplier at the moment Gohan turned into one, rather Raditz described it as a "manifestation of a Saiyan's true power". So I think it manifesting itself as Gohan's angry power (~1,300) works rather well. We see it obviously wasn't multiplying Gohan's normal power by 10, otherwise Oozaru Gohan would be less than 20 seeing as Gohan's normal was 1. Unless Gohan was afraid there like in the spaceship and was 710, making his Oozaru self at 7,100... dunno, I go with the first. The Oozaru seems to have a different effect on Gohan's power (perhaps due to him being a half-Saiyan?), in which Gohan seemingly doesn't have his normal power multiplied by 10. At Vegeta Saga, Oozaru Gohan was also much stronger than weakened Vegeta, while his normal self didn't even have enough power to move. The same in movie 3 (non canon, but fuck it), in which Oozaru Gohan seems weaker than Turles, whose power shouldn't be too far ahead 30,000 while Gohan's power base was 10,000, which would make his Oozaru self like 100,000 in the conventional way. Maybe it just unlocks Gohan's current hidden powers, whereas in a 100% Saiyan it manifests through a 10x multiplier?