Thanks for all of the replies, folks!
As far as the distance is concerned, we have now agreed on an eighth. Both of us felt that a quarter would favor me too much, as many of you mentioned earlier.
As far as pedals are concerned, I'm not sure. I tried clipping-in quickly on my ride yesterday, and while I didn't miss the clip, I still found myself wondering if throwing the flats that came with the bike (sans toe clips) on might be a good idea. His only chance is getting me is off the dig, so I doubt he will agree to a rolling start or letting me lean against something. We shall see...
The course will be a straight, flat stretch of road.
Regarding his fitness, at one time, he had excellent conditioning, but I don't believe he rides much anymore. Definitely not pro or even amateur BMX racing level. I'm pretty new to road cycling, but had a decent level of fitness before hand from kickboxing and weight-lifting. He will definitely be a lot lighter though, as I'm 6' 3", 200lbs.
Also, that "Shirtless Keith" fella looks pretty quick. I wouldn't like my chances against him 😜.
I'll try to get this done this week, and will post video, as well as GPS, as one member requested.
Updates to follow...