What about this scenario:
In Season 18, sell some players and keep just enough of them to finish 7th.
With the money you got, you can buy one more trainee for cheap (like 4k Superstar for 100k) and start training him and two other young players you already have. Invest other money into Arena.
Until you can, try to win cup games and lose most of league games. When you are out, try to win away games so you get attendance on home games.
In the meantime, invest money into draft and a bit into Arena, while trying also to save a bit (remember, you have cheap team - slightly above salary floor).
Try to find your next superstar in the draft.
Win the relegation matches and in season 19 see what you get in draft. If you get a great player, keep him and sell the now 19yold superstar trainee for profit (he should be worth at least 300-400k then). If you get a not-so-great player, sell him for few bucks (again, 200-400k). Either way you get money.
When you are done with that, inspect the league and see if you can promote if you save enough to buy one or two good vets right before playoff to help you carry you to the championship. If you can't, wait and save one more season and in S20 you will have enough money to promote.
So the plan consists of getting out of D.III in two or max three seasons with nice trainees and bigger arena. That's at least how I'd do it. Actually I will do it in S19 when I will train my Point guards on C position to make them into SFs.
EDIT: Btw, don't try to sell your players now. Try to sell them in first weeks of next season. Yes, you will pay their salaries once or twice, but until you sell them for more than now, they will help you with the cup.
Last edited by Koperboy at 10/25/2011 3:15:25 PM