Catched up to Paper Mario: TTYD streams, and I dislike how helpful the chat was being. If Ben is going to the wrong direction, forgets/doesn't know about a game mechanic, or asks something, then I feel like it can be good to say something, but telling him hints and tips unprompted gets a bit annoying. If he misses an item, badge, or a star piece, so be it. If he decides not to equip the cricket SFX badge before Hooktail, I think he should be let to fight Hooktail without it.
In this case he did ask just before the boss fight about if he'd missed the cricket badge, because he hadn't realized what the sound effect was supposed to be, but people told him to equip the badge way before that, and that's the point. I would find a more natural playthrough a lot more interesting than one in which he might as well keep a GameFAQs tab open. TTYD isn't even a hard game anyway. Maybe at the very end it can get a bit tough.
Ben seems to be enjoying streaming/playing the game, though. I guess that's the most important part.