Not necessarily, I remember in season 15, a team that just won Div III promoted, wasn't doing so good, half-way in the season bought cheap veterans (30+ yo) and won the division. I think experience plays a big role as I didn't think his team was very good through the roster. That or our division at that time was weak.
So yea in the long run it might hurt him but since he's selling and buying old and not training them, it doesn't really matter. The only negative I can see maybe is that it's gonna cost him money to constantly buy and sell unless he breaks even every time.