I gotta go with Pyramid or Super Password (I'll narrow it down by the time I finish this post). Even with a team of writers, crafting a question takes work...I've done it for various people's games as well as a "home version" of a game I put together called Countdown. Don't even get me started on the wordy questions Barry and Enright used to ramp the drama. Each producer had his or her own style of writing, though...
For a trivia game like $ale or Jeopardy!, you're prolly looking at a good 30-40 for the former (including Fame Games and the Speed Round), and 61 for the latter. My hat always goes off to the writers who compile your generally "difficult" trivia (a $2000 level clue on J!, anything in the upper tier on Millionaire), or even the riddles on Jackpot. However, I'm with Chris in the fact that I wouldn't mind getting the hard work out the way, then enjoying the rest of my week.
Granted, coming up with seven subjects for a category on Pyramid is no walk in the park either. It's not so much the fact that you gotta come up with seven items...it's coming up with seven items one can describe quickly. In the case of SP, you gotta have five good words that can be described in just one word. All that being said, I think I could have enough fun with Pyramid, and would love trying to come up with good Winner's Circle topics. So yes, Pyramid. :-)
Off the board, Split Second or Double Talk. Now, am I just a head writer, or do I get promoted any point? Can I pitch my own show to the network after certain milestone years? ;-D