@Sono
Tails is pretty much a prime example of what a sidekick should look like; all too often such come off as cheap, contrived tools rather than unique characters. Hell, I didn’t even catch on to the whole engineer angle in the Genesis days (unless they just added that later), but that still left a shy, loyal orphan with a birth defect that allowed him to fly (which I guess is super powers in a nutshell, or at the very least Marvel’s brand of mutants, and I think early on they tried to market Sonic as a superhero), and at least back then he stood out (although I could also say the same for Shadow). In fact, AI aside, I think everybody was glad to see Tails; I know I was.
Also, concerning the “pressure” you speak of, Tails did have that coming-of-age character arc in SA where he struggled to “fly solo” (even though nearly all of his levels ironically require you to beat Sonic in a race before that even came to a head, plus he did have a couple of his own games on the Game Gear). Actually, in one scene I think they actually hinted at Tails feeling under appreciated.
…as fun as the humor in the modern games are, and as much as some fans will insist that Sonic doesn’t need a story (even though the Genesis games, especially S3&K, clearly had one), I actually miss the days when the characters were
characters, that were part of something bigger than going from point A to point B and made the lore relevant (I mean, for crying out loud, the Chaos Emeralds aren’t even in Sonic Boom, whereas SatAM at least had something
like a Chaos Emerald (largely to explain where power rings come from) that the Archie comics basically retconned with actual Chaos Emeralds, just sayin’). Yeah, okay, so SEGA’s saga may not exactly be Shakespeare, but it has had moments where it shined.