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I mean you'd have to spend a lot of time working out the exact way the "daisy chain" would work, but age limits might be something to look into. If you get these guys coming in via historical minors and set a minimum age of, say, 23 for the MLB league that might be one way of having this happen.
To be more granular, you could set minimum AND maximum ages for the college league so they stay there for their allotted time then "graduate" into the MLB.
HS is a no-go. It isn't worth the hassle with so few guys in the OOTP database being of HS age. But I did this with a College league feeding into the MLB and, while there was a lot - a LOT - of fiddling about, it worked. They stayed until the stipulated age in the College system then, at the end of the season where they passed the threshold, went into the MLB Draft and away they went.
The biggest hurdle is that OOTP gives the MLB first dibs, it reigns supreme over all leagues under it. So you'd have to devise the Draft scenario to somehow work for you so that the college-aged players go into the College Draft and the older guys straight into the MLB one. not sure how you'd do that.
I have some notes lying about for the league I did. If you want to pursue further hit me up on PM and I'll shoot them through.
Hope that helps
G
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