I'm mainly a Gale fan. I figure he can be a little awkward at times but it makes sense given he's been isolated for a year and didn't have friends before that. His bragging doesn't bother me because from the bottom of my heart I do not believe him lol. I immediately took it as a front where guy's trying to make himself useful in an irreplaceable way. Makes sense when Gale sees himself as personally worthless at best, an imposition or burden at worst. I don't even think the orb incident was an act of hubris (he wanted to have personal worth to Mystra the way she had personal worth to him--reasonable in a healthy/equal relationship) and I genuinely don't think it's something he needs to be forgiven for. ESPECIALLY when Mystra's a former mortal herself. I don't think what Gale did was morally wrong. Just tragic and naďve.
I didn't take much of it as bragging tbh (apart from the obvious bragging parts) but as fun childhood anecdotes - you can meet both of the creatures he summoned after all - which he uses to befriend you and persuade you that he is more use than trouble. Persuasion is after all his dialogue proficiency so it makes sense he uses it with you - and with Mystra. It's odd how this act is sometimes held against him "because he should have been happy with what he had" isn't defying the Gods the main content of the game? And aren't many Tavs gobbling up special unique buffs and powers right left and center?
In general, I don't like how patronising the player dialogue gets when talking about power. In Gale's case, when you discuss his plans of not-quite-godhood with him two of the options are something along the lines of "I love you for the man you are are, not the god you'd pretend to be" and the usual "power corrupts" both feel very moralising to me (the "pretend" is bothering me in the first one). At this point the characters have had enough brushes with the gods to give you a multitude of arguments against Gale's plan. I would have loved real arguments based on previous experiences, as they would have helped to show your connection through the experiences you shared. A discussion based on reasonable arguments would also feel more suitable to convince an INT-based character like Gale.
There are also a few moments in which I'd like an option to take his side or at least talk to him afterwards. There is this moment you can get with Lorroakan on the no-godhood path, which makes it pretty clear that Gale's Folly has also made him a bit of a laughing stock in the academic community. This was previously only hinted at at best (It certainly puts a new light on his year in solitude.) and it's a topic worth a discussion, if only to check if he is alright after the scene.