Ill keep it to FM08
Worst player ever signed - Stewart Downing for Liverpool. spent about 12 million and he was consistently average and didnt help at all
Best player ever signed - no question about it, well actually its a tie...Lauri Dalla Valle for 30k (turns out hes my best player) and Alex Fernandez on a free, both for Accrington
First player you normally sign/scout on a new game on any fm/cm - really, its Alex Fernandez. He always, always delivers.
Best achievement on fm/cm - FM 07 - Getting Accrington to the Premiership
Worst moment on fm/cm - quitting way too many jobs XD
and for FM07 (though dont remember much)
Worst Player - Gustavo Varela for Liverpool
Best Players - Freddy Eastwood and Darius Henderson for West Brom, both got me 25+ goals a season
First player to scout - have no clue

Best Achievement - West Brom into the Champions League, India to the World Cup
Worst Achievement - trying to put Toronto FC into the game, starting it, and failing miserably