As long as the theoretical relationship began in the second arc (when both of them would have been consenting adults), the age gap isn't bad. Weird? Maybe. Bad? No.
But as long as it started in the second arc, the problem is definitely that their personalities are very different. Yeah, maybe they're both cowardly, but the one difference is that Greatness is selfish, and would rather risk her whole tribe than her own scales. Starflight, as we observe in The Dark Secret, is not like that at all and despite his cowardly nature, he still managed to help Glory save both the NightWings and RainWings from total destruction.
(Greatness would never do such a thing. She's loyal to her tribe and kingdom, yes, but to a limit — that limit being "does it harm or affect me in any way?" And in which case, she'll give up the lives of her tribe for an instant.
I suppose you can't really blame her, though. Her mom was horrible, her father was nowhere to be found, she didn't seem to have many friends, and she was suffering her whole life from the volcanic island. I wouldn't be surprised if her mental and physical health both is greatly diminished — also, it's not like her tribe is huge, nor are any of them very nice or morally correct dragons.)
We also don't know very much about Greatness or her background. Did she have any siblings? Did she know her father at all? Was she bullied for being un-princess-like? We have no idea. Starflight, on the other hand, is a character we know LOTS about. It's a big difference in information, and that topped off with their differences in personality, it's fair to say it's not the best ship ever.
It could make for an interesting plot in fanfiction, though. Maybe that's why people ship it — not because it'd make for a genuinely interesting or stable relationship, but because it's good fanfiction material.
That's my best guess as to why people would ship something like that, anyway, lol.
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WoF ships
FantasiThis does include my opinion, but it's mostly addressing the canon ships and the debatable ships, and basically the ship wars in the community.