Also same, this seems to be related to https://en.wikipedia.org/wiki/Dyscalculia

I am just apparently very bad at estimating which hand is the longer one (if there's not a huge amount of difference). Once I figured that out... reading the time is not a problem.

Do you where one strapped to your body at all times? If you did, I bet you'd find it more intuitive.

I wore an analog watch for about 15 years and never hit the point where it was easier for me to read than a digital display.

Same for me. My house had loads of analog clocks when I was growing up, I had one for a watch for over a decade, but still it was always a little bit harder to figure out than digital for me.