Sync iPhone between iTunes on PC and Mac?

My brother-in-law is a paraplegic and I am trying to help him sync his iPhone (original) with his iTunes. He has a MacBook (Black) but when his hard drive crashed he started using his old Dell laptop and iTunes. Apparently, this is what he originally sync'd his iPhone to. He now has his MacBook back and wants to sync his iPhone to this. This is not a problem with his purchased iTunes music library but he has some music from his CDs on his Windows iTunes and this machine is in Florida and he currently is on Cape Cod.
When I connected his iPhone to his MacBook, a dialog box popped up saying that there was new software for the iPhone and his iPhone music library will be erased.
Question: Is there anyway to sync his iPhone to both his Windows iTunes and his Mac iTunes without erasing the entire music library?

No, there is not.
The iPhone can only be synced to one iTunes library at a time.

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