I have to admit the only reason I have any affection for this style is because they’re the first Jill books I ever read. Looking at them now from the cold distance of adulthood, they really don’t appeal at all - and those eyelashes on the pony at the bottom left of Jill Enjoys Her Ponies. I think the portrayal of Jill is just about bearable, though where are Jill’s plaits? W D Underwood was better at humans than ponies, who are really rather awkward.
I will though always have an affection for Jill Has Two Ponies, as I think it was quite possibly the first Jill book I read. It’s one of the better covers from that series. I think it gives you a good idea of Jill’s relationship with Rapide, and it’s one of the better pony portrayals in the series.
W D Underwood is an illustrator about whom I have been able to find no biographical or other information at all.