I'd do what HPP suggests. I'm only in my second full season, but by buying low, training guys up, and selling high I managed to put a couple million in the bank, buy a level 6 trainer, and through the draft and transfer market acquire a couple young players to build my team around. Now I plan to sit near the bottom of Div III for a couple seasons while my young players improve, and then put the rest of the pieces I need in place to move up. I think the key is not to rush.
On a side note, the draft can be excellent when you're in Div 4 because there are so many bot teams and also new users who may not put much money into scouting. I had the last pick in my league last year after winning, but still got my top 2 choices.