From a risk perspective I would say co-signing a home mortgate for one of my brothers, but that's family and I'm not sure it really counts. I've helped lots of stranded motorists over the years either pulling/pushing them out of ditches or snow banks, jump starting their vehicles, drove one woman home (she was very nervous about getting in my vehicle but I handed her my cell phone and let her call her husband and give him my name and address from my DL to assure her it was okay) and one time drove four miles back to my house to get 5 gallons of gas for a woman who had run out on the side of a country road with her children with her and had no money for gas, a tow truck etc. These are all pretty minor things but I think if we all do what we can in those types of situations the world is just a better place all around. There are a lot of times I see posts in neighborhood groups asking for help with an appliance, electical issue, etc. and I think "I could go help them with that" but unfortunatly the litigious society we live in makes doing so way too risky anymore so I don't.
I've helped friends with pinball machines but that's just part of the hobby as far as I'm concerned and I always get beer or borboun out of it.