Structurally, your comparison reminds me of the different ways of searching between the old Yahoo style and google. I found reading an analogue clock seems similar with searching old Yahoo, which you start with the large group, then drill down to a smaller group for more details.(eg. time/min/sec) Meanwhile, a google search result and a digital clock tells you a pinpointed result right off the bat. It’s up to you to choose the information that you need.

Also conceptually, I think the analogue clocks are taking double representation or something. I assume the original design was derived from a sun dial with the shadow. The shadow is not actually time, but it’s a representation of time. Even before the shadow, the sun itself is a representation of time also. In that sense, the digital clock’s number present a stripped-down version of time and it’s representation is closer to the abstract concept of time.

And you’re right. Cognitively, to read an analogue clock, you need learn not only the system of time but also the system of the clock. There are angles, directions, two/three hands, numbers, (sounds familiar?) Further more, you might have trouble reading an analogue clock not because you have a problem reading the visual information of it, but maybe, you have been exposed to the numerical representation more than the visual representation of time. (eg. schedules, recording/playing devices, and etc)

On top of that, some peoples are just good with numbers ;)