Ya, I can see that. being a steve caballero fan since the early 80’s and old school skate dad i don’t know if i like the dragons more because they look cool or because i know one of my favorite skaters of all time designed them. I do like that indian says only 100 sets are produced.To be honest ... they are a bit too much for me. I like more the standard design.
In the case I would go for a theme based design (like the dagon here) on the bike, two points would be important for me: The theme should not only be on the airbox but also catched up on other parts like e.g. the radiator cover, the wheels, lamp mask, fender ... things should match together. The second point is: When I would go to have an artistic brush on my bike I would like one that is unique and will not be seen on any other bike.
But like always: This is completely a question of taste and if you like the design you should definitely go for it.