I'm looking at this from my perspective, asking myself how I would organise it (for Steve, not me - I don't have the legs to do it!)
My idea would be to have a group of helpers, each offering a 'base' where he could stay, who could feed him, wash clothes, charge things that need charging, download GPX files, and do basic mechanical bike maintenance.
They'd need to be spaced out far enough apart for Steve to get his wanted distance each day, and if the rules allowed it, how about seven bases, with seven routes, each leading to the next base?
Each base could have a spare bike, even if some had to be ferried about by volunteers.
This approach would mean that everyone got into a routine, and that would have to help....