Here's a thought: Seems like most of us agree that while there's probably room for improvement in several areas, it's not like the skateboard consumers of the world are all clamoring for some big problem to be 'fixed,' and especially not at the higher price point that such a thing would likely entail.
But most of us love trying new stuff, or have some amount of desire to dial in our setups for one particular purpose, feeling, aesthetic, etc.
What if the most meaningful technological advancement is not related to the products themselves, but rather to the was we design and produce them?
I'm thinking about the way that more people are starting to handcraft artisan decks. If it was easier to get the perfect shape and dimension that I wanted from a local guy with a small-scale woodshop, I would probably be happy to pay a few extra bucks that are going to stay in my local community. Again I'm reminded of surfing, and how local shapers can use templates or CAD files or whatever to basically imitate or modify any model you like.
Now imagine if the more manufacturing-intensive stuff like wheels could be made to spec as well. I would definitely be hyped if I could go down to my local urethane dealer and get some F4's custom made in 95a.
This would be more related to advances in small-scale manufacturing technologies, maybe tied to the rise in "makerspaces," 3D printing, and stuff like that. I think 3D printing as it currently exists is basically useless to skateboard gear, but it seems like the general concept of making new kinds of fabrication possible to end consumers could be really interesting.