This thread got me thinking and going back through some of my purchases. I thought Flintstones 2 was my most expensive, but after going through old messages it looks like I traded, so I am something like:
Flintstones 2 Surprise at Dino $625 (2013 - NA) (mix of cash and trades)
Little Samson - $450 (2013, ebay with $50 off?)
Spiker! Super Pro Volleyball - $450 (2019, ebay - cart only, was part of a lot including console, apparently I wasn't the only one who saw the cart in the picture...)
James Buster Douglas CIB - $355 (2015, ebay)
Bounty Bob Strikes Back - $325 (2015, AA)
I was so close back in the day to pulling the trigger on Stadium Events when it was around $3k, but my wife would have killed me, in fact, probably still would even if I got it for $3000 today! Probably the one piece I will never get, forever at 676.