How do weather services get sky conditions above the surface?

§ñühwØ£f writes:

I would a55ume that they have planes in the air at some point and the
aircraft report the ceiling height of teh clouds and then they estimate
windspeed from observaton stations on the ground.
I'm just guessing. I knew a weather observer once.

That makes sense. I wonder how they estimate things like heights and
distances, though. I suppose experience would help to come up with educated
guesses for these, but one might still be way off. Certainly experience would
be useful in recognizing specific cloud types and patterns.

One article I read (I think it was Wikipedia) mentioned just ten radiosondes
for the entire Caribbean, that's hardly what I'd call high-resolution
measurement. You could almost fit a hurricane between radiosondes.