[mention]Captain Cadaver[/mention]
Tenshinhan never said anything about having confidence in his abilities when it comes to fighting #19 and #20 and to assume Piccolo planned on being nothing but support like the humans would be pretty out of character for him.
Also, Ten was far more sceptical on the existence of the Artificial Humans in general, whereas Piccolo seemed far more believing in Trunks' validity.
He said he left Chaozu behind because he didn't think he could keep up, so unless Tenshinhan is being hypocritical, he wouldn't have come himself if he didn't find it worth it.
It was pretty out of character when he wanted Gohan to finalize Nappa and willingly put himself on a supporting role along with Kuririn then, right?
Yamcha was the one skeptical about their existence, Tenshinhan never doubted Trunks' words.
Because going up against a foe he's been told surpasses everything that came before head on is far less intelligent than being cautious against an opponent he can't even sense, especially when he didn't have a solid grasp on the limits of their power just yet.
Then how can Piccolo claim he's confident is he doesn't even have a solid idea of their power?
The Androids aren't exactly supposed to "surpass everything" - Trunks did claim Goku had a shot against them, so it's not a shot in the dark.
Immediately following up by explaining "I'm the one they want" so it being because Piccolo is incapable wouldn't be strictly correct.
That's not my point, which you left out. Piccolo didn't even question Goku's request, as if he didn't really mind taking a minor role in the fight.
Definitely seems like a case of initial thoughts vs conclusion. Again, there'd be no point in adding the "stronger than we realised" line if overestimation was purely the reason for Piccolo being able to tool #20.
Not really. Those he's fighting were two Red Ribbon Artificial Humans who appeared in the time and location Trunks gave, ready to kill Goku. For Piccolo to be capable of beating one of them, he either underestimated himself before or they overestimated these Androids. As per later statements, the later is the case.
There'd be no point in even wondering if Piccolo were so strong. In fact, it's impossible for him to have grown too strong, as the Androids were supposed to be a deadly match for the Super Saiyans as per Trunks' word, and Piccolo easily clobbered one of them. He's definitely overestimating himself trying to find an answer as to why things played out so differently.
Irrelevant when he was still compared.
Not at all. Kuririn claims Piccolo's like a Super Saiyan, Piccolo does a super power up, and Kuririn says that
now Piccolo is like a Super Saiyan? Doesn't compute. It's like saying 5x2 is still a 5. One of the two statements got to be false.
He never said that though. The most he said was calling Piccolo's fusion him becoming a Super Namekian, which was more of a way of saying he had a massive boost in power rather than him being on the level of the SSJs (which is incorrect when he had confidence both before and after Piccolo did so that he would surpass the SSJs).
He didn't only call him a "Super Namekian", he also compared him to the Super Saiyans:
Chapter: 355 (DBZ 161), P11.7
Kuririn: “If Goku and the others are Super Saiyans, then Piccolo will be a Super Namekian.”
It's certainly putting him on the league of the Super Saiyans, something that's redundant if he had already been on their league.
Indeed. He was a main villain who killed several notable characters, had major effect on Goku/Vegeta's history and pushed Goku into gaining a new transformation.
Taopaipai was also treat in high regard at the 22nd TB, despite all evidence pointing to the likes of Chappa being above him, and Kuririn used his reputation as the basis of him being concerned for Tenshinhan rather than him oneshotting Chaozu.
Main villains in Shonen who have an overbearing impact on the plot are often treat in higher regard than lesser villains who succeed them. For example, Hokuto no Ken having Shin, Rei and Souther treat amongst his greatest rivals in the Shura Arc despite Falco and Han surpassing them, or Arlong being used as a benchmark in the Fishman Island Arc of One Piece despite having been fodder for a long time. This makes sense because these rivals or villains had a personal impact on the characters and their growth either as a person or in their power and, thus, them being treat in high regard long after becoming fodder makes sense, much the same as why Freeza is constantly brought up long after his death compared to #19 and #20.
These are different situations, though. Tao's case is Roshi and Tsuru (Who didn't see Goku vs Chappa, mind you) being surprised Goku defeated Tao, rather than using him as a measure stick. It's also possible Tao in a all or nothing fight is more of a threat than Chappa in a tournament settling with rules, given he's a trained assassin with no scrupulous. The example from Hokuto no Ken is the maintance of an old rivalry, akin to how Vegeta still saw surpassing as his ultimate goal in spite of Gohan surpassing them both.
Freeza's being used as a benchmark to the new foes, with statements like "Even the Super Saiyans, who can beat Freeza, can't beat the Androids". The memory of how much of a challenge Freeza
was isn't relevant if he isn't one anymore. It'd be like if Kami said "Even Vegeta, who's far stronger than Nappa who killed you was powerless".