It's an interesting challenge, that's for sure, and an interesting puzzle to ponder. According to some websites, it's actually 320 miles, but let's go with 330 for the sake of discussion. If he is going to succeed, this thing is going to require careful planning.
Let's start by splitting the distance, 330 miles (~531 kilometers) in half: 165 miles (~266 kilometers) for each day.
The first day is going to be key for this guy. If he can manage that, his chances of completing the second day are vastly improved.
On a road bike, rider weight is distributed equally on three points: saddle, pedals, and handlebar. Maintaining this distribution of weight requires some effort. As the rider begins to tire, less weight is put on the handlebar and pedals, and more weight is taken by the saddle.
Let's say he maintains an average pace of between 12.5 and 13.5 miles per hour (20-22 kph). (Actually rather generous in this case, considering that the route will necessitate quite a bit of climbing.) At that rate he will be in the saddle for between 12.2 and 13.2 hours. (If he rides at 10 mph, as someone else suggested, he would be in saddle for 16.5 hours.) I'd give a reasonably fit, motivated, enthusiastic
non-cyclist about four to six hours in the saddle before he begins to flag.
At six hours he is less than half way through his day. Around that time, if not before, he will increasingly feel his shoulders and neck beginning to cramp, his hands and feet beginning to burn, and his bum subject to increasing pain. What was earlier a road bike now becomes a medieval torture device. What follows is six to eight hours of increasingly severe torture, which is a sure recipe for failure. And we haven't even got through day one.
What he really needs before he starts, in order to prevent this, is
miles in his legs. For this reason I have prepared a periodized training schedule. He needs to stairstep his way to 165 miles, so that by the time he gets there and needs to do it, he has reasonable assurance that he can do it.
For someone of his age and likely condition, it would be best if he could train three days on, one off; or, even better, three or four on and two off, over many weeks. But with thirty days to prepare, there isn't time for that. Instead, then, I start him out with three on, one off, and then from there go four on, one off. The final week in training is very light with lots of rest, so that his body has time to adapt and he arrives fresh.
I assume that as a heart patient he will have medical supervision. I also assume that with this medical supervision - and with Lance Armstrong at his side - he will have certain, erm, recovery aids. Frankly, there is no way he can do this without medical assistance, given his age and status as a non-cyclist. (And rather than hiring Armstrong, he'd have been much better served by hiring Dr. Ferrari.) Here is his thirty day training schedule (it begins in April, and his ride starts March 31, but just pretend the schedule began on March 1):
The only thing that gives me real pause about this extremely aggressive schedule is week three, where I have him doing, effectively, six centuries+ in seven days. But I am relying here on the
miracles of medical science for recovery - about which we won't say any more since this is not in the Clinic.
Assuming he has scouted his route, has a good support wagon and support riders, has completed all the necessary preparation, and followed a training schedule similar to this one, I'd rate his chances of success as quite high. If he's going to wing it, on the other hand, try to tough it out through sheer macho - and if he is prohibited from hitching a ride on the sag wagon - then I predict he will fail. So we will see if he succeeds or fails, and how he prepared or didn't.
PS. If anyone here with real expertise in periodized training has any corrective suggestions, or better ideas, I'd be happy to hear them.