Community challenges
Something that I feel would be really cool to add in the future would be 'King of the Road' type community events. Imagine if there was a week-long community challenge that had players choose between two brands/teams (e.g. Chocolate and Girl), and have to earn however much rep to unlock tiers on a reward ladder. And at the end, whichever brand/team has the most Rep wins, with the players who choose to "ride for them" during the event getting a special reward (e.g. board, title, clothes, etc.).
This would also be a really interactive way of introducing new brands to that game, which gives players a chance to get some new gear without having to pay money for in-game currency. I know that this will be somewhat addressed with the free Season pass, but I still think it would be beneficial for everyone to have some sort of system that rewards players with just branded apparel and gear, instead of knock-off and basic fillers like we have in the store and neighbourhood boxes now.
I feel that something like this would really liven up the Skate. community, especially with the inclusion of more free-to-play content that incorporates the brands and formats we all know and love.