Before my dh had surgery in October, I did a major first run blitz on tossing papers. (I knew that I'd get virtually nothing done for a couple of months.)
Recycled a whole bunch of greeting cards from many different occasions. I did save a few that had very sweet notes from people that mean a lot to me. And, there were many trips down memory lane just like you. How wonderful to find that note from your mother.
I chucked all kinds of old B&B info. Some of it hasn't changed much. I will be glad when I'm outside of the auditing window for a biz so that I can get rid of all the inn paperwork. It's getting close now...
Good luck with this project!!.