My FM2008 story. When I do a large quest like this, my goal is always to build a team up from nothing, build my reputation and aim to get offered a job with Leeds United (who I support)
Loaded up the English, Italian and Spanish leagues to do a big managerial quest. Hit randomize and got a lower league Italian team called Monopoli. I did ok with them getting them promoted to Serie B after 2 years. Got offered a job with Walsall who were in the Championship at that point. I took that job, got fired after one season as I got them relegated (oops).
Sat around unemployed for a few months applying for jobs all round the place. I got offered manager position at Val Di Sangro. Italian Serie C2. I got promoted to Serie C1 in my first season. Spent a few seasons there in mid table but had an amazing Coppa Italia run in which I dumped out Lazio and Udinese and reached the final against AC Milan who hammered me 3-0 with a Wayne Rooney hat-trick.
By the year 2029, Val Di Sangro had won the Coppa Italia, Won Serie A twice. Won the Uefa Cup, Also beaten finalist in Uefa Cup and got to the Quarter Final of Champions League.
I still follow Val Di Sangro in real life now and like to see them do well. Sadly in real life they got relegated to Serie D group F which is not featured in Football Manager. Last season they got so close to promotion losing on the last day of the season. Currently sitting 15th in Group F, having a terrible season.