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Sounds like you want random players - not just those from a particular point in time - for your start-up, not just for rookies, right? If so, then your league sounds very do-able. But you'd probably want to get some advice from some of the guys - like David Watts - who has done a lot of Random Debut leagues...
My advice with things like this is always to start off with a test league. Set it up minus the facegens, logos, ballparks, etc. (or at least don't spend significant time on those), and just let the game play out for at least a few seasons. Don't immerse yourself yet. Then, once you've proven your concept - the game is turning out the way you want - start over for real and begin your immersion. This way, you won't get a few OOTP years in, after investing a lot of time & effort, only to find out that something is not to your liking that could only have been corrected at setup...
Good luck!
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