There are scanning apps that automatically crop the photo, let you make multi page PDFs, and automatically upload to your cloud of choice or directly to your computer. This has made it super easy for me. I've tried a few and settled on the one-time paid version Genius Scan and it works well for me.
I played for the first time in 2008 as well! Played hard for the next 4 years of undergrad then laid it down for grad school, got back in for a couple of years in 2016-2017, then life got busy. I haven't bought the steam version yet, but when I saw it coming out last year it looking like the dwarf fortress i always wanted! Can't wait to start playing again!!!
I carry a Leatherman Squirt PS4 in my pocket every day. It's tiny and doesn't add bulk to my pocket but is super handy and I use it all the time. Has spring loaded pliers and tiny scissors, a small straight blade and file, and both a flat Phillips head and broader flat screwdriver.