We had this challenge with my grandmother. I had some really memorable moments with her late in her life, but she looked a lot sicker and run down in any pictures from that time, but that's how I remember her (at least that's part of how I remember her). My mom didn't want to share as many pictures from that phase of her mom's life though because she remembered her younger and more active, so it made putting a memories collage together complicated. Especially since all the early pictures were still in albums spread across the country with her children.

Personally I want people to use pictures of me that let them remember me the best. Not the best of me, but the best of our relationship, even if that's me as an ugly old fart.