And if you want a couple episodes to see if you want to bother with the franchise at all, TNG's "Darmok" and DS9's "Duet" are the place to start
I would start with a best-of of The Original Series (TOS), then the TOS films, then The Next Generation (TNG) and Deep Space 9 (DS9). Voyager (VOY) if you want. TNG, DS9, and VOY are collectively called the TNG era, which is what most fans consider core Trek.
Until it stops breathing
No, just his taste. He clearly enjoyed being on Seth MacFarlane's shows.
Edit: checked MacFarlane's twitter 
Crusader Kings
I've been saying this since the very first trailer used the word "crusade"
Good luck! I'm making more!
Pit borg discourse
I've understood that I'm agender for a long time, I just thought that's how everybody is and I had to play along with what I saw as fundamentally conservative bullshit. My egg cracking was realizing that gender is a real thing people feel and not just genital astrology.
This is why he's doing all that corruption, to get Trump to notice him?
"The Hormuz Crisis", the left is calling it, but do you know what I heard? Many people - very cool, very hardcore people - they're calling it "the Dark Souls of commuting and buying food". It's time someone told the casual Democrats that it's time to get good!