As it was said before: Oda has to remind himself about who Usopp really was and how to develop him. I think that Usopp spending with Heracles those 2 years instead of being just by his own broke him too, since Heracles was that protector of the jungle and as he met him he hit the spots with his thinking perfectly for Usopp, making him role in that imagined picture of a hero, feeding that imagined picture of himself. Heracles was just exactly what in theory was Sogeking, but for Usopp's development in negative way. I don't say that he is a bad character, but pairing him while those two years with Usopp was a bad idea. He could have been somewhere else on another jungle like island to make Usopp think about his past self by looking at him, showing how much he overcome and developed as a person. Dunno I think if Usopp would be left alone for a while to reopen some of his wounds and cores in his mind to survive would be great for him to have, at least in that theory.
He build his character on fitting to people's liking, being that jokester and all, instead of focusing on himself because from my own experience I perfectly know he don't want to focus on it because if he will think into it deeper he will be more and more depressed. Hitting that down point can destroy or fury and motivate person to work. That is exactly why he just don't want to be left alone. And that is why Water 7 and Enies Lobby was so great for him because he could just reflect on himself and take his shit together. Franky was a great pair for him at that time, because he gave him options what could ruin him but on the right moment to instead lit the fire in him, same is with giving advices.
In conclusion: he needs instead of a hero figure, a villain figure to truly become a greater himself.
Plus despite being a coward he has that bravery in himself, he just need a moment of a lesson to find that golden spot when to be brave and when a coward.
He build his character on fitting to people's liking, being that jokester and all, instead of focusing on himself because from my own experience I perfectly know he don't want to focus on it because if he will think into it deeper he will be more and more depressed. Hitting that down point can destroy or fury and motivate person to work. That is exactly why he just don't want to be left alone. And that is why Water 7 and Enies Lobby was so great for him because he could just reflect on himself and take his shit together. Franky was a great pair for him at that time, because he gave him options what could ruin him but on the right moment to instead lit the fire in him, same is with giving advices.
In conclusion: he needs instead of a hero figure, a villain figure to truly become a greater himself.
Plus despite being a coward he has that bravery in himself, he just need a moment of a lesson to find that golden spot when to be brave and when a coward.
