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As long as you're able to ask the owner for good things like more money, the owner should also be able to butt in and make you do bad stuff or give you tougher missions in mid-season ("we spent tons of money on this guy and you put him in the minors, get him up and see what he can do", "This is the team's 100th anniversary and we want you to try to beat the club win record this year", "we need higher attendance, get some more popular players in there").
To be honest, the game can already be fairly easy for solo players - asking for more money in mid-season unbalances things in the wrong direction.
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