Yes skateboarding needs progression, as do all things. It is the nature of existence; nothing can remain, ultimately chaos reigns.
Sure there's bigger rails with more kinks, or bigger stairsets with bone-breaking drops, but it's possible we may be looking at this all wrong - We're still thinking within the current paradigm, failing to comprehend beyond our own comprehension.
Without making a wild prediction I can't really say what the future holds, but I can guarantee that it is so different that it brings into question this thing we call "skateboarding" in it's entirety. I don't believe the solution (or rather, the future of our culture) lies in brute-forcing the human body to do increasingly more fucked-up-shit, I mean, it's no secret that "creative", low impact, "aesthetic-based", skating is on the rise, and possibly even the default / most widely accepted style of skating at the moment, especially within the younger generation.
With that in mind, I wildly predict that skateboarding will become steadily more abstract, with video parts blurring the lines between art, promotion and self expression further more. Nyjah's gonna start doin freestyle pogos in his SLS run getting the first ten-club. Video parts will be edited, scored, performed and written by the skater to enable more autonomy over the creative direction of the piece. Tim Pool will buy SLAP, making us the Forefathers of the First Establishment of Skateology. Life will go on.