"Inscribed" items, items made out to someone, are not as valuable in re-sale as "signed" items...items simply bearing the autograph of the artist.
I'd much rather have a nice autographed photo -- "Sincerely, Barbara Cook," for instance -- than one that says, "For Wendy, a sweet fan. All my love, Barbara Cook".
If an item is going to stay in a family, then, yes, the inscription will have much meaning for the heirs. I would imagine that a back story would add to the value of an inscribed item on "Antiques Roadshow". But in general, getting a signature on a photo at the theater door, or at a signing, it's potentially more valuable to eschew the personalization for future value.