Just to pose a little discussion on this topic . . . I think that winger is one of those places that you can take quality over quantity. Have you seen what wingers go for on the market? How about this for an answer . . .
In the interest of metric assloads of cash . . .
Train 10 midfielders this year, however train Reg as an IM when training Playmaking and train him as a winger when you are training winger. Fill that final training spot with a 'Day Train' candidate that you don't plan on holding onto for more that 1 season and have him swap out with Reg when you make the changes in training. Just a thought.