I have no context for why they are discussing battle plans, but I'm sure there are plenty of fanfics this could fit into. The designs are from a SUPER old drawing I did back when the fandom was still active (with a few minor alterations). Gosh, I drew that 6 years ago... maybe I should do a side-by-side comparison.
Hiccup, Toothless, Jack (c) Dreamworks
Rapunzel (c) Disney
Merida (c) Disney/Pixar
Honestly, I was never really "in" the fandom, but I was definitely around when it was huge lol and would reblog people's art of them because people got REALLY creative with it! So I have a soft spot for "the Big Four," and thank you for still creating content for them! <3 This is beautifully done!
I only ever got in the fandom because the fanart was so creative. I remember I was trying to find reference pictures for Jack Frost and these random pics with the other three showed up lol.