Another way is to add other parametres to the draws and weigh all those. The draw shouldn't be based solely on the average quality of your 14 best players. Factor in the net worth of the club including your cash and you would come a bit closer to fair draws.
It's an intertemporal choice in order to trade off costs and benefits at different points in time. What we're basically doing is exchanging one asset for another at the end of the season and then switch back at the beginning of the next. We sell human capital (players) in exchange for financial capital (cash) to trick the drawing. Then we exchange back by buying back aforementioned human capital (players) for financial capital (cash).