Not sure this thread really belongs this forum, though. Seems almost as if it would have been a better fit in Future of Trek or Fan Fiction.
I'd say it fits more in Future of Trek.
To answer the OP, having all five captains or crews meet wouldn't work well. However, if you didn't try to shoehorn Archer and Kirk into the plot, a TNG/DS9/Voyager crossover movie might work if it was well written and well directed. Actually, an adaptation of Star Trek: Destiny would kinda fit the bill and could be as successful as the book series or moreso.