I started with Yeovil Town (I like a challenge). This has been an insane challenge because you have no assets to start. Your training facilities suck, your stadium only holds 9,000 (of which only 5,000 is seated), and you only have $100,000 to work with initially to make transfers.
2006: Managed to stay up in League 1 with a 15th place finish
2007: Gained promotion to the Championship by finishing 2nd
2008: Stayed up in the Championship by finishing 11th.
2009: As of right now (Feb I think) I'm in 5th place. No way I'm going to finish top 2 because Ipswich and West Brom are running away with it, but I have a legit chance at grabbing a playoff spot. If I do, who knows...maybe I can qualify for the Prem.
In that time I've managed to sell enough players to fund a stadium expansion (now holds 11,500) and improve training facilities from below average to good.
The most annoying thing about playing with a small club is that it's impossible to hold on to the badasses you find and nurture. I've got 4 players on my first team that are constantly getting attention from the likes of ManU, Leverkusen, Valencia, etc. It's just a matter of time before I have to sell them because they demand a transfer or I lose them on a free because they won't sign a new contract.