[Pdubya64]

DE:
One of the hardest concepts to grasp and then not forget in OOTP is how the scouting system works (also a good reason to pay attention to stats!).

The analogy I have settled on is that every single head scout has on his own particular pair of "Rose-colored glasses" (Google it if not familiar) when he looks at players. As chazzycat says, tools vs. ability comes into play, along with the basic yardstick of the HS's rating. Obviously a low-rated HS is going to "miss" more often than a better one. Then there is the overall GAME setting for scouting accuracy. You can set it where it is perfect (not much fun in my estimation) to downright crazy random.
At the end of the day, trust the stats, make a few bets on your HS's reports if he is pretty good and trust your instincts, then develop it as you play the game. Just realize there are a LOT of underlying "cogs" that make the big OOTP Player Development wheel go 'round.

Try not to get too frustrated.