Making choices is hard because, if you make wrong choices, there is a real possibility of bad shit happening.
Newsflash. The player is not clairvoyant. He cannot know that in the game there are no uses for, e.g. Medicine skill but are plenty for Diplomacy.
It's ok if the player has made a dumb decision - went into a diplomatic situation with an Expert Surgeon that cannot into social encounters. That's consequential and I think Josh agrees it's commendable, However, the game should provide content for his Expert Surgeon built as well - because that's what the skill was for. Sure out character won't be able to intimidate some bandits, but he will excel in other places a diplomat would be hopeless at. There should be content out there on the virtue that mechanics was implemented.