IDK, you can rise pretty fast in some of those organizations. I'd also be more concerned about player development investment than actual competitiveness. Good players escape bad teams eventually. And good prospects on the juggernauts often get traded to teams like the ones you list.
Yeah, more or less this. But Pittsburgh's development is pretty uneven, especially if you're a pitcher. Same story for Kansas City. Nats would be down there just because their development sucks, again especially for pitchers. I wouldn't want to be a hitter drafted by the Diamondbacks.
For the same reason, Oakland wouldn't be awful; and other than the stadium, the Bay Area is pretty nice. Cleveland would be a good place to be drafted because of the development, even though it ends in Cleveland.
