I just stumbled into this — in October 1967, IBM published this problem in Eureka, the journal of the Cambridge University Mathematical Society (page 2):

The triplets (whose abilities at walking, cycling, and donkey riding are identical) always leave home together at the last possible minute and arrive at school together on the last stroke of the bell.

They used to walk the 4 1/2 miles, and so had to set out at 8.00; then they acquired a bicycle and found that they did not have to leave home until 8.15 (Charles rode it for the first 1 1/2 miles, left it, and walked on; Donald walked 1 1/2 miles, cycled 1 1/2 miles, and walked again; Edward walked 3 miles and cycled the rest). More recently they have been given a donkey. After experiments to determine the donkey’s speed and to verify that it stood stock still when left, they found that — using the bicycle and the donkey — they did not need to leave home until 8.25. There were several schemes of changing over which they could use to do this, of course; but naturally they chose a scheme which involved the minimum number of changes. Going to school tomorrow Charles will start on foot and Edward will arrive on foot. How far will Donald walk?

In place of an answer they listed the address of their London office, as an invitation to prospective systems analysts. I can’t see that they ever published a solution to the puzzle; I’m posting it here for what it’s worth.

07/01/2024 UPDATE: Reader Catalin Voinescu supplies the solution:

Riding the bicycle for 1.5 miles takes 15 fewer minutes than walking the same distance, so the bicycle saves 10 minutes per mile (compared to walking).

Another way to look at it is that riding the bicycle 4.5 miles saves three people 15 minutes, or an aggregate of 45 person-minutes (see ‘man-month’, another concept popular at IBM at the time; ‘The Mythical Man-Month’, an excellent book by Frederick P. Brooks, Jr, explores this in detail).

Riding the donkey 4.5 miles saves a total of 30 person-minutes, or 6 2/3 minutes per mile (compared to walking).

It’s not possible for any person not to change means of transportation, because they would arrive too late (walking) or too early (other means of transportation). For the same reason, it’s not possible for each person to change only once, because whoever got the bike and the donkey and did not walk at all would also arrive too early. Thus, the minimum number of changes is four, with one person walking and riding the donkey, another person walking and riding the bike (not necessarily in this order), and the third doing all three.

The person who walks and rides the bike needs to save 25 minutes, so they need to ride the bike for 2 1/2 miles and walk 2 miles. Assume they do it in this order (see below). The person who switches twice needs to ride the bike for the final 2 miles.

The person who walks and rides the donkey needs to save the same 25 minutes, which, at a rate of 6 2/3 minutes saved per mile, means 3 3/4 mile of riding the donkey and 3/4 mile of walking. They have to walk first and then ride the donkey, because the person who switches twice needs to ride the donkey for the remaining 3/4 mile, and they can only do this at the beginning (we already have them biking at the end).

The person who switches twice rides the donkey for 3/4 mile at the beginning, and bikes for 2 miles at the end. In between, they walk the remaining 1 3/4 mile.

So: Edward bikes 2 1/2 miles then walks 2 miles. Donald rides the donkey 3/4 mile, walks 1 3/4 mile, then rides the bike 2 miles. Charles walks 3/4 mile, then rides the donkey for the remaining 3 3/4 miles.

If we assume the person who walks and rides the bike does them in the opposite order, we get a mirrored solution: Edward rides the donkey for 3 3/4 miles and walks 3/4 mile; Donald rides the bike for 2 miles, walks 1 3/4 mile, then rides the donkey 3/4 mile; and Charles walks 2 miles, then picks up the bike and rides it for the remaining 2 1/2 miles.

In both cases, Donald walks 1 3/4 mile.

Other solutions exist, but they require more than four changes. It’s even possible for the three people to each walk, ride the donkey and bike equal distances (1 1/2 mile of each, each), but I don’t know what minimum number of changes that would require (more than six, and not all 1 1/2 mile stretches can be contiguous).

(Thanks, Catalin.)