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.