[takinola]

There's an old episode of RadioLab or This American Life (I can't remember which) that explores this very topic. If memory serves, there was a woman who lost her mum at an early age but her mum recorded videos to be shared with her at certain points in her life (birthdays, graduations, etc). I recall her mentioning she came to dread those events knowing she would have to relive losing her mum by watching the video. I can't recall if she felt it was a net positive or not.

[borbulon]

I wish you could remember more, I'd like to listen to that

[AlexErrant]

Possibly not what OP was thinking of, but maybe this one https://www.thisamericanlife.org/283/transcript

Ctrl+f "video"