If you play the market smart, your buying power will always go up. Buying at 25 and selling at 30 is not smart. If I buy a player low during the offseason and sell the player high before the playoffs next season, at the bare minimum I would be able to buy a similar player low in the next offseason to continue the cycle. More likely I turn a good profit since I bought low and sold high, which increases my buying power. Also, this does not consider the other sources of income I have generated over the course of the season.