I think what we really missed out on was a worthy Star Trek The Next Generation film. There was more evidence of ambition and creativity in the episode Yesterday's Enterprise than in all of the four films combined. They should have been able to transport the drama and the intelligence of the series into a two and a half hour long space epic. Like a science fiction Dark Knight.
For example, imagine a cinematic Best Of Both Worlds. You have a wonderful story that can be told with a much greater budget and much more time. You would have had more time with Locutus, you would have seen Wolf 359. Then the next film could have been a direct sequel - a reworking of First Contact. At the end of the Best Of Both Worlds film you see the cube blowing up but releasing a small vessel and Captain Riker following it back with the Enterprise and Picard's life is in the balance in surgery etc. It would have kicked the absolute crap out of The Empire Strikes Back. It goes without saying that there would be no Borg Queen or Android sex nonsense in First Contact and that the film would actually be about something.
I know they couldn't have actually done this because of continuity etc. The point is that the films actually lacked the scope of the most dramatic episodes in the series and that really baffled me.
By the way, Star Trek 2009 was a terrible film.
What I hope for is a new series that would be a true successor to The Next Generation. It would be set a generation after Picard's.