Hubert has blond hair and a green shirt. He's in a snowy area, but you'd never be able to get there without having Fox lv1.
Yep. You can talk to the "gray guy" even twice to get the armor delivery job even if you haven't talked with Hubert first. He delivers the I don't want to talk to you line but puts the armor into your inventory after second click and then asks you to take them to Hubert.
Actually I tended to stumble on a lot of stuff in reverse, too. I got artemis as my first bow upgrade because I ended up stumbling on all the necessary companion power ups before getting the lower tier bows (Tapio was the only better bow I got after Artemis).
Thanks for spotting the bug. I was just missing a check, so that's been fixed now.
As for getting inconsistently powered bows, it's because the game isn't linear. I think there is still another better bow you can get, just that there isn't a scenario so far that leads up to it yet because it's not implemented.