Honestly I think that the one-note strong personalities most NPCs and side characters have is part of the charm and making it more dialogue based would kinda ruin the vibes and pacing it has. That being said however I do think that the Winters segment was lacking. The only two characters we really get to know are Tony and Andonuts, and while both are great I think we needed more time at the boarding school. Characters like Maxwell who are supposedly important to Jeff just don't really leave a mark and we spend way more time in the forest with Bubble Monkey than with the supposedly important people in his life. The best part is when you finally get to his father because I really feel like I understand Jeff and his upbringing. That small interaction they have gives more depth to him than the rest of segment and it makes me sad we don't get more like it.
I hope it isn't too horribly sacrilegious to critique Earthbound, I do love it and it's tied for my favorite game ever. I just feel Jeff's segment is lacking compared to Paula and Poo who get wonderful inductions.