I have actually completed two separate 3 way pinball trades. One was so convoluted, I don't even recall some of the trade items involved. I know I gave a pac-man upright and some NES games along with money to someone that had a pin I wanted that was in turn going to trade the NES stuff to someone else for a different pin they wanted (different amount of money as well). That person also had a Neo Geo game I wanted so it got thrown in the mix as well. It took a month to get the details and transactions all worked out.

On the easier to remember 3 way trade, IJ-CV-G&R-TSPP and $ all traded hands across two states.

I took crazy to mean difficult and complicated. Not "best deal" type. I have put the "best" deals I've got in other threads but have really only made a few trades over the years... none of which favored either side tremendously.