Oddly enough, I can only remember the stupid things that DH has done that have cost us money / been a right pain in the ass.
Got on a train, insisted that we put the bags in the overhead luggage rack.. got off the train without the bags.. including 3 new pairs of expensive kids snow boots.. we were short of cash at the time, it hurt.
Key stress: DH moved the car keys from my bag to his, without telling me, totally stress me out until he told me. He then managed to lock the keys in the car.. had to break a window to get in.. window had radio antenna wires in it.. cost nearly €350 to replace.
DH insisted on buying a sports car for our wedding.. I loved it at the time, less so when we lost £8K on it 2 years later when we had to sell it as DS came along and it was a 2 seater.
He has also left house keys on the train... had to break a window to get in.. passports in a hotel because he insisted on sleeping with them under his pillow rather than just leaving them in my bag, passport and boarding card at the scanner in the airport, passport in the seat pocket, expensive watch at a campsite wash hand basin, phone in a seat pocket on the plane... I still have to stop him moving my things and putting them in overhead lockers, in his bag, in safe places when we are not at home. At home it is me who can never find my keys, wallet, phone but those dramas while stressful have less expensive consequences.
Wow.. that was therapeutic!