As a collector of many multi-signed items, I can say for sure that group items 99% of the time sell for less than the sum of their parts. It's just an unfortunate reality for most except for very significant items.
This ball could be special. Having Bush on the ball would have really sealed the uniqueness of it for any collector as likely a one of a kind item that would have tied the ball to the event more closely. I do think a letter from your dad explaining the provenance may be enough to get that extra value out of it. Maybe more than $500.
I would get it certed just prior to when he is going to sell it by whatever company is considered the most reputable at the time. I would think this would be the type of ball that would do well in an auction with a big write up.
As an aside, any chance he still has contacts and could get Bush to sign the ball now? I think it def would be worth it
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