Part of the difficulty though is you have to "put yourself out there" and get a little out of your comfort zone in order to gain experience. Take the mentioned crosswind landing for example, how do you develop your skill if you don't progressively accept higher and higher crosswinds? Flying IMC I think is another area. You get your ticket, maybe never having been in real IMC, and need to take baby steps to build your skill/confidence. To go out and try an approach when the tower report is the weather is on the minima on your first real IMC in command flight would be crazy, but with practice comes confidence, and you can work your personal minima down to the published.