So, you can play Windjammers online with GGPO (someone kindly pointed this out in an early thread about windjammers). I just set it up to use with my PS3 controller and it controls really well and feels great, but I have only played offline at the moment.
moderator edit ) This site will provide the details to download the emulator and its online component. From there you should legally obtain a ROM of windjammers, which if you are like me, you just ripped your cart of windjammers.
Should we try and get a bit of a league going? I haven't tested this online yet as there are no other players on the Windjammers chat room so I may be totally wrong about all this but it does seem possible. Also GGPO supports money puzzle exchanger. So there's that.
EDIT: GGPO may not support money puzzle exchanger.