Delixe: Well 2011 is the most newcomer friendly so far however it's still brutally involved. Your assistant manager can be set to handle a lot of things for you however how effective he is depends on his ability. There are a lot of websites out there to help like
FM Info,
Sort it out SI and Sports Interactive's own forum are pretty helpful.
At the end of the day I am going to say YMMV. Football Manager will give back as much as you are prepared to put into it. I would suggest downloading the demo on Steam first but you may be overwhelmed by the sheer amount of data there is. All I can say is if you are prepared to learn how to play the game and prepared to put in hours (and I do mean weeks and months really) then you will find Football Manager to be the most deep and involving Strategy/Management game there is by a huge margin over the competition.
Thanks for the advice. I am downloading the demo now, and I'll see how that goes for me.