I must admit I'm in the negativists corner over FM08 (It's pretty much unplayable and the out of the box version should have been slammed by reviewers) but I've never experienced this.
I always put my past career as "Former semi-pro footballer" and moving up is pretty easy. In my latest game I took Southport to the title in the first season and was mid table in the conference national in the 2nd season when Crystal Palace, bottom of the Championship came calling. I managed them for 14 games until I was sacked and I, strangely got the Charlton job with 3 games to go in the second season and finished 8th in the Championship.
I got promoted with them the following year and at the start of the Premiership campaign (4th season) I again jumped ship and joined Man City. Another one and half seasons, this time around 2nd in the
Prem, but without winning anything and I was given the Roma job.
There is another side to the OP. I probably didn't deserve the Palace job, certainly didn't deserve the Charlton job and was lucky to get the Roma job.
May I suggest that your problem lies with managing a low reputation club? For example had I stayed with Southport until they were in the Championship, would a Premiership side have taken on a manager with no big-club experience?