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I was just thinking, how about the option to retrain players from a young age to make it their default, and for them to 'forget' their old position?
For example, Ashley Cole, who was originally a striker and is obviously now a left back. I believe John Terry used to be a striker too, but I'm not sure on that one. I'm sure there are other examples out there.
It's just that when a 15 or 16 year old comes through your ranks, it doesn't always means he'll play in that position for his whole career. Particularly if you manage to get a young centre-back who's got good anticipation and is a better finisher than he is a marker, you might look at him and think "Oh, he'd make a decent striker with a bit of training".
Maybe in coach reports it could state "Ass.Man suggests that it may be beneficial to retrain Player X to centre forward" or something.
I tend to do that with certain potentially good youth players. Nothing as extreme as Strikers to Left-Backs, but certainly Wingers to AMC, or MC to DMC. Whatever I need for the formation of my team really.
I remember in FM06 I had players coming through my youth setup who had no "Natural" position, just a position in which they were "Competent" or occasionally not even that level. I've not seen it in FM08 though so maybe it was just a bug. In those cases you could retrain them and they would forget their supposedly best original position.