Top 3 :
1) selling my grew up stuff when playstation 1 came out. I wish I kept everything and still have my child’s copies of zelda, Marios, punch out, contra, FF3, Chrono Trigger and everything else..
2) selling almost every CIB and sealed NES/Snes games I found from 2000 to 2005, including a sealed copy of M.U.S.C.L.E that I remember - still have the other copy that I’m glad I kept! I had no money and had to resell to refund the money I spent buying those lot of games and be able to keep a few of them.
3) reselling my SE Star Keepers copy as an auction on NA for around 30-40$ more I paid, just a few month after I bought it.. I talked to the buyer months ago, he still has it and will let me know someday if he want to sell it..
Also, I wish I took more pictures because I don’t have picture or list of that stuff from the past..