I don't think you mentioned what the item was, because in my view that makes a difference.
If it was a rare one of a kind item, I would probably keep it as-is.
If it is a more common item, I'd send it in and get it signed. Even if the sig is poor, it still passed through his hands, and ultimately that is more important than having a textbook perfect signature.
As a collector I have a long list of regrets from waiting too long on any number of people. Other than items that went missing and never returned, I can't think of one regret from sending an item.
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