Been there with the OCR mess. I spent like three hours searching for my grandma's maiden name in some Ohio paper from 1912 and kept getting hits for saddle soap and corset ads. The old news sites scan the pages at such low quality that letters like S and F get swapped all the time. One thing that helped me was searching with wildcards or just the first few letters of the name, plus trying the paper's own site instead of the big database. Also sometimes it helps to put the name in quotes with a year range, since the search engine will pick up close matches even if a letter or two is wrong.

The part about how "he just stared at me" is funny but idk if the takeaway here is really that deep. Kids are confused by everything from our past, that's kind of the deal with kids. My niece asked why we had a phone book and I didn't walk away feeling like the 90s were some lost simple time, she's just 9 and phone books are weird now. The pager ad thing mostly tells you that stuff gets dated fast, not that life was better before algorithms. Those ads weren't simple either, they were annoying on purpose so the jingle would stick in your head, that's the same trick every ad uses today just with better targeting. Maybe it's just me but the confused kid reaction is more about them being a kid than about us losing something.