There's a really simple solution that ensures Kyle will play A Link to the Past: tell him grandma got it for him. Bam, now he has to learn to appreciate and love it. :)

Probably not the worst (thanks MadCatz PS1 memory cards!), but my most recent big one was the Witcher 3. I stopped playing about halfway through last year and picked it back up a few months ago and finished up the main story. Started Hearts of Stone, stopped playing again.. and then the Blood & Wine release date was announced. Unfortunately, it was around the same time that my Windows 10 install started to act up. When it comes to unexplained Windows errors, I've got a scorched earth policy that has worked quite well for me (aka reformat). Unfortunately, I forgot that my copy of Witcher 3 wasn't on Steam but on GOG Galaxy, which does NOT backup saves to the Cloud. :(
That's a LOT of time down the drain.