I would think he is less likely to be noticed with an expired license then if he had none. in fact having none might make it look even more suspicious. either way, if he is stopped and having no title it might be seized on the spot with everything in it and sent to police impound yard until it clears the stolen vehicle background check through the last registered legal owner and he says its not stolen. if the last legally registered owner wants it back, then its his to pick up and leave with and your dad is SOL that's why you never buy ANYTHING without a clear title, even if its from a sweet little old lady or a priest.
your dad needs more to prove ownership beyond a simple bill of sale and he will be taking a big chance taking it out on the road in its illegal state and I hope he didn't buy lawn art if the title cant be sorted out.
good luck with it
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