Crossover stories with 'How to Train Your Dragon' often start from the dragons themselves, I've noticed. They're such versatile creatures that writers can slot them into nearly any setting—medieval fantasy, sci-fi, even modern-day worlds—and it somehow clicks. A story I read recently dropped Toothless into the 'Avatar' universe, not the blue people one but the elemental benders. The writer spent pages just on Hiccup trying to explain why a Night Fury wouldn't violate conservation of energy when shooting plasma blasts, which was oddly fascinating.
What makes these blends work, or fail miserably, usually comes down to whether the writer respects the core feel of both worlds. Hiccup's ingenuity and Toothless's loyalty are the emotional anchors of 'HTTYD'. Plop them into, say, the grimness of 'Game of Thrones', and you get a tone clash unless you carefully adjust. I've seen brilliant fics that treat it as a culture shock comedy, and awful ones that just want dragons fighting White Walkers. The good ones find a shared theme, like found family or overcoming prejudice, and build the whole crossover around that.
Lately there's a trend of crossing with pirate or naval stories, 'One Piece' or 'Master and Commander' stuff, which makes perfect sense given Berk's Viking seafaring roots. It feels less forced than some random insertions.