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While the conversion won't be perfect, the conversion was tested. So, it's not like it is going to be a major issue, IMO. You might have to start over so to speak, but the changes aren't drastic enough for me to consider it starting over.
Now, in your case, it just might be. If every version to version conversion has say 6 small issues, then when you convert through several versions like you'd have to, then you would experience them all at once and it would seem like a major issue.
If I were you or your commish, I would talk to folks in leagues that have converted through each version. There are leagues still out there that have converted all the way from OOTP 3 or 4. The Baseball Maelstrom is one that comes to mind as does the USBA.
It would be bad business-wise if OOTP couldn't convert version to version. That means the conversion needs to be solid.
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