Ok I managed to lose two more games by putting the GK on the field, and a DMC in goals. That should work ;p
As for your questions. Money is not a problem because the first season, I am in both CL and Cup so making tons of cash. As for the league, win or lose you still play 26 games. The second season, I won't be in the CL (since I tanked the previous season) however, I will not be buying new players either since I will still have the same team. Then the cycle starts again.
I hope it is a fun way to play this game because I would rather build a team over two months rather than doing it over and over again every month. Beside, it is not like there is any advantage in increasing levels.