David,
Not sure how you catalog and keep track of who is who at these things
(as you do them) so that you can sell the print to them in the first
place, but I'm sure you have some sort of system.

I can't tell you how to go back and locate your prior files, but I
would suggest that to avoid this situation you follow up each sale
with a post card or letter within a year or so, offering them the
digital file on CD for $xx. You could even use this situation to
explain that it is impractical to offer reprints into the indefinite
future (when memories slip) and so this is their ONLY opportunity to
purchase the digital image.

This may be anathema to some, but I think for this sort of photography
business it would generate a pretty good percentage of income over and
above what you were doing before. People who have purchased from you
in the past are more likely to do so again in the future, and if you
only offer it to those who originally made a print order, then you
aren't really hurting your real-time print orders to generate the
addition income (from fear of losing the image for all time, if they
don't purchase it now). I'd give it a value-added name like Legacy
Images.
: )

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