I'm still working on this, but
Kirk vs. Picard? Kirk.
Spock vs. Data? Spock.
I used to be a huge Next Generation fan, but I've gone old school over the past couple of years.
One thing I like is Star Trek novels featuring the characters from the original series. It's totally dorky, but fun. I just finished reading one based on that episode where the planet's going to be destroyed and Spock and McCoy end up going back thousands of years in time and Spock reverts to wild Vulcan ways and snuggles with Mariette Hartley. The premise of the novel is that Mariette subsequently has a son and Spock must somehow go back into the history of a destroyed planet to reclaim him. And other stuff happens. It's really good.