Thanks, Slowhands, as ever. The pdf you've pointed up is pretty informative and this article from Australia in 1923 is nicely surprising. But, like other material, it's thin on facts prior to arrival in London.
I have found a reference to a booklet, described on genuki as "well-researched", self-published by Michael Whittington of Coates, Cirencester, and entitled "The Whittington Story", ISBN 0 951351 0 1, in which in the first four chapters might be helpful. But I can't find anywhere to get hold of it.
Interestingly however, www.historyofparliamentonline.org/volume/1386-1421/member/whittington-richard-1423 takes it as read that Dick was the third son of Sir William Whittington, a "minor Gloucestershire landowner" (bit of a slap to the area there!) That website in turn says its content relies heavily on C.M. Barron's "Richard Whittington" in "Studies in London History," ed. Hollaender & Kellaway, which does show up on Amazon for example, but again I suspect "London history" may not have much to say realiably about the Pauntley bit, so I'm reluctant to shell £16.95 or so.
It would be fascinating to discover more about his early days. If it's true that Sir William Whittington had been outlawed for marrying Thomas de Berkeley's widow without the appropriate consent, and that Dick was the third if not later son, then despite the widely accepted connection to the "minor" Pauntley Court it may well be true that Dick Whittington arrived in London in modest circumstances. However, if so, he may have run a good line in sob stories. It seems clear that he racked up such a massive fortune in a short time from sales of gold cloth that he was able to bail out the monarchy. Perhaps he had decent funds when he set out after all.
The folk tale says his early employer in London encouraged servants to place one item for good luck with the master of a ship before it set sail, and that Dick thus gave up the cat which he had bought for one penny to keep the mice down in his attic room. The ship, the "Unicorn", reached a hitherto unvisited place which was overrun by rodents, whereupon the local ruler, learning of the cat's prowess, bought it for megabucks which the master promptly handed over to Dick when the ship conveniently docked back in London shortly after Dick had peformed his campanologically inspired u-turn. I think this says more for the perceived honesty of sailors than for the accuracy of the record and I don't believe a word of it.
I live down the A24 these days. Avoid it in the rush hour, or you may never pass beyond Burford again.