I posted these points a couple of months ago and nothing has happened to make me change my mind. I still think that Kurt's (relatively) last-minute decision to take part in this event left him under-prepared. Indeed, I'll go further. I reckon Kurt's competitive cycling normally relies on a lot of other people: those who organise long-distance races and ensure that the rules are applied and also well-equipped support teams. Alicia is doing a great job driving him about and looking after his food, but it seemed that he had to take time out for visiting bike shops.
To get the kind of support that is required needs either a lot of cash or a lot of goodwill. Steve has a huge amount of the latter, quite simply because loads of people have ridden with him and he has been prepared to give people, effectively, free hands-on courses in long-distance cycling. That also seems to have generated sufficient of the former to get him by, with a bit to spare.
Obviously, my only knowledge of Kurt is from his participation in this event, but he has clearly cultivated an "elite" image. That's not, in my view, going to get people to put themselves out for you. I doubt very much that Kurt's racing schedule allows him the time to ride with the ordinary, and less ordinary, folk who make up Steve's wide-ranging support network.