If you are into board games at all, I would highly recommend Fleet Captains. The common consensus among reviews is that it is "a season of Star Trek in a box." Considering the number of miniatures that it comes with, it's a decent price.Getting started on my top 738 episodes and films... but it might take a while to rate the whole range of novels, short stories, games, and comics from the beginning.
My experience with Trek beyond its cinematic form is perilously inadequate. I fully intend to remedy that this time around. (I rewatch the bulk of the shows every 4-5 years, always with that thought in mind. This time my rewatch has been more thorough than ever, including shows/films I haven't thrown into the blender since initial airing and whatnot, so I'm all the more prepped and ready for it.)
I identify myself as a bit of a gamer (mostly story-driven stuff, though) but the only Trek game I've ever gotten to spend much time with was Birth of the Federation. Lovely 4X-genre title, that one. I'd probably include it by the time my list hit 60 or so.
I've read a total of about 15 Trek books, meaning I've got so very much ahead of me. I'm really looking forward to it.
I've dabbled in the board game scene here and there; I've just been waiting to get enough folks who are into the same stuff I'm into to come together and throw down on something like this. Fleet Captains sounds pretty stellar, and I've slowly but surely expanded Trek's influence on my core group of friends, so I'll look into it sometime in the near future. Thanks!