BA, you put waaaay too much thought into this. get some sleep.
if anyone here has checked out the ratrodbikes site, they have build off challenges all the time. it's a friendly way to goof off with someone you only know as an internet penpal.
if you want an informal build off, just say what you want, find the guys who'll go for it, and then, just build it.
that being said (typed,) i'll challenge anyone to a vintage old timey build off.