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I'm not sure exactly what you're asking, but you shouldn't have to start over. If you have a database that was using v4, then your league went to OOTP5, when you open that database in v5.2, it will do the necessary updates to work. Now, you want have all of the extra data that v5 is bringing in, but you'll have a working database.
I guess if you're saying that in order to get all the new data, you have to start over, then I guess that's correct. But, you don't have to start over. You could consider the earlier years to be similar to the early years of MLB where there is not as much data as there is for more recent years.
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