As much I like Normal Guy all things considered that charms The Winter Lord by being dorky and on the spectrum (you can’t say that Jack isn’t looking at Hiccup all doting like when he is rambling) that eventually gets so dragged into the magical world he eventually becomes a spirit because Man in the Moon for once didn’t want to make Jack angsty.
I think a take that could be pretty fun to play around with is magic used to be more active back in time. People actually believed in these things but modern times has lessen the power of magic to mainly kids or the very spiritually inclined.
This means, Hiccup is actually Gifted/Touched and could possibly become a full on witch if he wanted too (Though I wouldn’t be shocked if he does do some very minor magic and just think it’s luck, mainly dowsing via the land itself guiding him places he needs to be). It’s why magical creatures like him. And taking inspiration from Jack Frost's Declassified Transdimensional Travel Guide to Love (and other Souvenirs), Hiccup with some guidance probably can interact with nature sprites as long he is shown how to actually communicate.
Pretty much, he can’t be a Merlin and do actual magic himself but I won’t be shocked if Hiccup has always been well liked by the supernatural. He probably had a family of nisse that always showed where he lost things as a kid. Or probably the numerous times he got lost and was saved by some tall pretty lady with antlers and a ox tail and hollow back that disappeared when they reached Berk. (Huldrafolk my beloved).
Like Hiccup is so loved, the soil sometimes becomes soft when he decides to lay down his head. Or the Wind practically adopting him and loving to play with his braids, even worse when he starts flying on toothless (Hiccup has no idea he’s so loved that in the skies he is practically always safe), or flowers have slight rivalry with each other to see which one Hiccup decides to smell absentmindedly.
Like Stoick was so concerned that Hiccup would eventually met a malicious being that will not be so kind so he probably had Gothi close off some of his magical connection to protect him. Otherwise he probably would be taken by a supernatural being to be their son or their groom when he’s older. Stoick was getting gray hairs. Which is why he spent most of his life unaware until he met Jack right when the protections faded and bam Jack like the other supernatural/magical beings immediately is charmed by Hiccup. Hiccup unknowingly has Jack wrapped around his finger.
Like lowkey, when he was being shunned by the village for being hiccup and not Viking like, he was practically full on adopted by the Wind itself. Playful but supporting gales when he was crying and everything. Pretty much claimed him and told the rest of the magical world “This boy belongs to the skies. He belongs to us. We shall give him the freedom he seeks.”. Which is probably how he eventually becomes The Wind Spirit after he dies as a human being.
