Obviously, you skip guys, you have high risk of signing, like Jeter publically announcing, he would only sign with the Yanks.
I think the signing structure for the picks, does take some of the risk away, of being able to sign them, once you draft them.
But, you still have risk for the younger ones, like the high schoolers, who decide to play college ball.
I get what you say about cant miss position vs pitchers, I guess there is so much more demand for pitching, and shortage in the market, requires you to take more of them in your draft.