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Challenged by 
to make a thread revolving around how I compare these characters, so let's start.
It's obvious that post-Karin Goku >> Taopaipai and that's where we begin. By the time of the 22nd Tenkaichi Budokai, both Roshi and Yamcha are concerned for Goku's matchup against Chappa, believing even a victory will be hard fought.
Chapter: 114, P14.1-4
Context: Goku’s first opponent in the prelims is King Chapa.
Yamcha: “So that’s King Chapa, huh…? Poor Goku… To have to face such a tremendous opponent right away…”
Kuririn: “Who’s this King Chapa?”
Yamcha: “He’s said to be an incredible master…It seems that when he last participated, he won the entire tournament without once being struck by an opponent…!”
Kuririn: “Whoa…”
Yamcha: “Th-this could be bad… Of course, it is Goku… If he’s really on, he may squeak by…”
Chapter: 115, P1.2-3
Jackie Chun: “Mmm… King Chapa, eh…?”
Yamcha: “Mr. Chun…?”
Jackie Chun: “Son Goku has certainly found himself in a sticky match right from the very start…”
Yamcha: “Indeed…”
Both of them are then shocked that Goku beat Chappa so easily and Kuririn even believed Goku must've had to use his full power and some reserves to take down Chappa.
Chapter: 115, P10.2
Context: Goku defeated King Chapa.
Jackie Chun: “That was simply…unbelievable…! To stop himself in midair…with a blast of expelled air…like a bomb…!!”
Yamcha: “I…I didn’t think anyone…could defeat King Chapa so easily…!”
Chapter: 115, P10.3-6
Context: Goku defeated King Chapa.
Goku: “I did it! I did it!”
Kuririn: “Be careful, Goku! If you put everything you’ve got into it from the start, you’ll wear yourself out!”
Goku: “But I didn’t put anywhere near everything I’ve got into it. If I did, he’d be dead. I wish they’d hurry up so I could fight with real strong guys like you all!”
Yamcha: “R-right… Hahaha…”
Jackie Chun (thinking): “Th-this could be bad…for me…”
This would suggest that 22nd TB Goku (Yamcha's expectations) ~ Chappa > Post-Karin Goku.
As for how Yamcha stacks up, there is a lot of evidence to suggest he and Kuririn would be above Chappa as well. One statement from Ten during his battle with Yamcha would suggest he wasn't expecting this much power from any of the three.
Chapter: 117, P7.3-5, 8.1
Context: The first round of the 22nd tournament began with a ferocious exchange of blows!
Kuririn: “Wh-whoa…!”
Goku: “They’re both amazing--!”
Announcer: “Wh-wh-what happened?!! All that action…and so fast…!!!”
Yamcha (thinking): “I…I never imagined he’d be so good…”
Tenshinhan (thinking): “Interesting… Evidently he wasn’t just full of hot air after all… It’s been some time since I encountered such formidable resistance…”
He later cites Yamcha as likely being the best of the three, despite having likely seen Goku's match with Chappa.
Chapter: 118, P14.1
Context: Tenshinhan won the match with Yamcha.
Tenshinhan (talking to Chaozu): “Don’t be complacent. Of course, this Yamcha was probably the best Kame-sen’nin has to offer…so it’s already plain that I’ll be the champion…and you’ll be runner up!”
Goku citing Yamcha as "amazing" when not offering the same to Chappa is also very telling. There's also Roshi's statement regarding their chances.
Chapter: 115, P14.2-3
Kuririn: “You were watching?!”
Kame-sennin: “Yup! All three of you displayed your progress magnificently! Any one of you may win the top prize this time!”
You could say this was just encouragement, but I doubt it would be entirely so, considering neither Yamcha or Kuririn seemed to be doubting their chances until after Yamcha's defeat against Ten. This would suggest that whilst Goku's displayed power was still above them, it wasn't by a level they couldn't combat. This is expressed further by Kuririn still having confidence in his chances against Goku, as well as Goku declaring it was the most fun fight he'd ever had.
Chapter: 125, P3.3
Context: said before he fights Goku
Kuririn: “I’ve trained really hard since then too…I can definitely win! I’m gonna do this!”
Chapter: 126, P4.1-2
Goku: “Amazin’! You’ve gotten better!”
Kuririn: Hihhih! Are you surprised?”
Goku: “I’ve never had such a fun fight! I’m really excited!”
So, overall Kuririn ~ Yamcha >> Chappa >/>> Post-Karin Goku >> Taopaipai.
Now, for arguing against/debunking some counter arguments.
"Taopaipai was still treat with relevance by Tsuru Sennin and Roshi to the point they believed Goku beating him was unbelievable."
In Roshi's case, I believe this would be due to his reputation, as we have no indication the two ever met. With Tsuru Sennin, it could be some bias towards his brother, plus he quickly turned around after only seeing Goku speedblitz a 21st TB tier fighter like Panputto.
Chapter: 122, P12.3-6
Context: after Goku defeats Panput
Tenshinhan: “That wasn’t one blow. While brushing off his opponent’s fast punch with his right hand, with his left he showered him with…3 rapid-fire elbow blows…That brat, he’s no ordinary person.”
Tsuru-sennin: “I see…maybe he really did defeat Tao Pai Pai…”
Tenshinhan: “This tournament is finally getting interesting…”
That and considering the mountain of evidence suggesting Taopaipai to be far below Kuririn and Yamcha, it could be taken as being about as relevant as Freeza stating he didn't believe anyone could surpass Ginyu.
Furthermore, you could argue that perhaps the lack of decent challenges, coupled with him not being too much younger than Roshi/Tsuru Sennin (he was 2 at the time of Daimao's rampage) may suggest that much like Roshi at the start of the series compared to his younger self, Taopaipai's strength had rapidly decreased by the time he fought Goku.
"Roshi was just judging Chappa by reputation."
Leaving aside the double standard in this being just as evident with Taopaipai, this would've become evident had it been the case. The fighters at this point in the series can easily discern a characters' strength from their movements, such as Yamcha immediately seeing Jackie Chun had improved from the 21st TB, so had Chappa not lived up to the hype by the time he used with Hasshu-ken, we would've seen one of them state something along the lines of "I guess his strength was overrated", yet we clearly didn't.
"Goku had the most fun against Kuririn because he was his friend."
Fighting against a true enemy has never affected how much fun Goku's had in a battle before, since he constantly makes note of it even in dire situations, such as declaring his excitement when first facing Vegeta or upon hearing that there existed a villain stronger than him (Freeza).
So yeah, don't believe there's much that would contradict the chain of Yamcha and Kuririn being far above Taopaipai at this point.
to make a thread revolving around how I compare these characters, so let's start.It's obvious that post-Karin Goku >> Taopaipai and that's where we begin. By the time of the 22nd Tenkaichi Budokai, both Roshi and Yamcha are concerned for Goku's matchup against Chappa, believing even a victory will be hard fought.
Chapter: 114, P14.1-4
Context: Goku’s first opponent in the prelims is King Chapa.
Yamcha: “So that’s King Chapa, huh…? Poor Goku… To have to face such a tremendous opponent right away…”
Kuririn: “Who’s this King Chapa?”
Yamcha: “He’s said to be an incredible master…It seems that when he last participated, he won the entire tournament without once being struck by an opponent…!”
Kuririn: “Whoa…”
Yamcha: “Th-this could be bad… Of course, it is Goku… If he’s really on, he may squeak by…”
Chapter: 115, P1.2-3
Jackie Chun: “Mmm… King Chapa, eh…?”
Yamcha: “Mr. Chun…?”
Jackie Chun: “Son Goku has certainly found himself in a sticky match right from the very start…”
Yamcha: “Indeed…”
Both of them are then shocked that Goku beat Chappa so easily and Kuririn even believed Goku must've had to use his full power and some reserves to take down Chappa.
Chapter: 115, P10.2
Context: Goku defeated King Chapa.
Jackie Chun: “That was simply…unbelievable…! To stop himself in midair…with a blast of expelled air…like a bomb…!!”
Yamcha: “I…I didn’t think anyone…could defeat King Chapa so easily…!”
Chapter: 115, P10.3-6
Context: Goku defeated King Chapa.
Goku: “I did it! I did it!”
Kuririn: “Be careful, Goku! If you put everything you’ve got into it from the start, you’ll wear yourself out!”
Goku: “But I didn’t put anywhere near everything I’ve got into it. If I did, he’d be dead. I wish they’d hurry up so I could fight with real strong guys like you all!”
Yamcha: “R-right… Hahaha…”
Jackie Chun (thinking): “Th-this could be bad…for me…”
This would suggest that 22nd TB Goku (Yamcha's expectations) ~ Chappa > Post-Karin Goku.
As for how Yamcha stacks up, there is a lot of evidence to suggest he and Kuririn would be above Chappa as well. One statement from Ten during his battle with Yamcha would suggest he wasn't expecting this much power from any of the three.
Chapter: 117, P7.3-5, 8.1
Context: The first round of the 22nd tournament began with a ferocious exchange of blows!
Kuririn: “Wh-whoa…!”
Goku: “They’re both amazing--!”
Announcer: “Wh-wh-what happened?!! All that action…and so fast…!!!”
Yamcha (thinking): “I…I never imagined he’d be so good…”
Tenshinhan (thinking): “Interesting… Evidently he wasn’t just full of hot air after all… It’s been some time since I encountered such formidable resistance…”
He later cites Yamcha as likely being the best of the three, despite having likely seen Goku's match with Chappa.
Chapter: 118, P14.1
Context: Tenshinhan won the match with Yamcha.
Tenshinhan (talking to Chaozu): “Don’t be complacent. Of course, this Yamcha was probably the best Kame-sen’nin has to offer…so it’s already plain that I’ll be the champion…and you’ll be runner up!”
Goku citing Yamcha as "amazing" when not offering the same to Chappa is also very telling. There's also Roshi's statement regarding their chances.
Chapter: 115, P14.2-3
Kuririn: “You were watching?!”
Kame-sennin: “Yup! All three of you displayed your progress magnificently! Any one of you may win the top prize this time!”
You could say this was just encouragement, but I doubt it would be entirely so, considering neither Yamcha or Kuririn seemed to be doubting their chances until after Yamcha's defeat against Ten. This would suggest that whilst Goku's displayed power was still above them, it wasn't by a level they couldn't combat. This is expressed further by Kuririn still having confidence in his chances against Goku, as well as Goku declaring it was the most fun fight he'd ever had.
Chapter: 125, P3.3
Context: said before he fights Goku
Kuririn: “I’ve trained really hard since then too…I can definitely win! I’m gonna do this!”
Chapter: 126, P4.1-2
Goku: “Amazin’! You’ve gotten better!”
Kuririn: Hihhih! Are you surprised?”
Goku: “I’ve never had such a fun fight! I’m really excited!”
So, overall Kuririn ~ Yamcha >> Chappa >/>> Post-Karin Goku >> Taopaipai.
Now, for arguing against/debunking some counter arguments.
"Taopaipai was still treat with relevance by Tsuru Sennin and Roshi to the point they believed Goku beating him was unbelievable."
In Roshi's case, I believe this would be due to his reputation, as we have no indication the two ever met. With Tsuru Sennin, it could be some bias towards his brother, plus he quickly turned around after only seeing Goku speedblitz a 21st TB tier fighter like Panputto.
Chapter: 122, P12.3-6
Context: after Goku defeats Panput
Tenshinhan: “That wasn’t one blow. While brushing off his opponent’s fast punch with his right hand, with his left he showered him with…3 rapid-fire elbow blows…That brat, he’s no ordinary person.”
Tsuru-sennin: “I see…maybe he really did defeat Tao Pai Pai…”
Tenshinhan: “This tournament is finally getting interesting…”
That and considering the mountain of evidence suggesting Taopaipai to be far below Kuririn and Yamcha, it could be taken as being about as relevant as Freeza stating he didn't believe anyone could surpass Ginyu.
Furthermore, you could argue that perhaps the lack of decent challenges, coupled with him not being too much younger than Roshi/Tsuru Sennin (he was 2 at the time of Daimao's rampage) may suggest that much like Roshi at the start of the series compared to his younger self, Taopaipai's strength had rapidly decreased by the time he fought Goku.
"Roshi was just judging Chappa by reputation."
Leaving aside the double standard in this being just as evident with Taopaipai, this would've become evident had it been the case. The fighters at this point in the series can easily discern a characters' strength from their movements, such as Yamcha immediately seeing Jackie Chun had improved from the 21st TB, so had Chappa not lived up to the hype by the time he used with Hasshu-ken, we would've seen one of them state something along the lines of "I guess his strength was overrated", yet we clearly didn't.
"Goku had the most fun against Kuririn because he was his friend."
Fighting against a true enemy has never affected how much fun Goku's had in a battle before, since he constantly makes note of it even in dire situations, such as declaring his excitement when first facing Vegeta or upon hearing that there existed a villain stronger than him (Freeza).
So yeah, don't believe there's much that would contradict the chain of Yamcha and Kuririn being far above Taopaipai at this point.
