Interesting.
1. Mark Lemmon, who posts here from time to time, went to IM Hawaii a number of years ago even though he did not qualify, and did what he called SoloMan during IMH race week. He wrote about this a few times in Inside Triathlon. It was good reading.
2. I agree with others that it woul be the run that would be challenging. Bike and swim would be OK. Just make sure that the bike route had a few places to stop to buy provisions. I would set up a run look of between 5 and 10 miles that had a few places to stop to get food/water along the way and you can carry some with you in a water belt or CamelBack.
3. The other strategy would be to get someone to follow along in a car and just hand up food/water when needed. This way you could be a bit more adventurous with route planning.
Fleck
Steve Fleck @stevefleck | Blog