Seattle is an example of a place which is generally cloudy, with infrequent clear days, so if you want clouds go there.
Table Mountain in Cape Town is famous for its frequent orographic clouds.
There are places which often get a marine fog layer, which is a type of cloud.
You can look at a satellite image and see a front coming through, as the band of clouds moves. If you are in Iowa and see there's a front in Colorado, then you'll be getting clouds pretty soon.
Hurricanes have rain/cloud bands which rotate around the center. Here too you can see that a band is coming, and predict where clouds will form.
Some parts of the world have a rainy season where nearly every day the clouds build up in the afternoon, with a downpour, and then clear up.
Noctilucent clouds, for example, can only be seen from latitudes of 45–80° both north and south, and they form around 75–85 kilometres above Earth’s surface, at the top of the mesosphere, the highest part of our atmosphere.
https://www.skyatnightmagazine.com/space-science/climate-cha...
Perhaps you might enjoy https://CloudAppreciationSociety.org/ (no, it's not about data centres).