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I have a 60 team league in it's 136th season and I haven't made any financial adjustments since it started.
Your post got me curious to do a financial checkup on the league and I noticed 7 of the 59 ai teams finished with a balance in the red last season, and of those only 2 are also in the red midway through the current season. They seem to work themselves out of the red over time be it getting out of a bad contract, or trading away a salary player or whatnot. It's like in the MLB some teams manage money better and it fluctuates.
On the flip side, some of the ai teams I have seen had some sweet rosters pieced together for multi-season playoff runs.
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"A passion for statistics is the earmark of a literate people." - Paul Fisher
"Baseball isn't statistics. Baseball is (Joe) DiMaggio rounding second." - Jimmy Cannon
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