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Hmm. Do you really need clouds? Don't you think they distract from the more important part - the foreground?
Or maybe I just envy your sky painting abilities
If (a very big if indeed ) I could figure out a way to paint a sky with smooth transitions from the lighter blue to the deeper, then yes I think I would probably go for the cloudless day look.
Aha yes, I always like to watch Bob Ross at work. He primes his canvas with a special paint called "Liquid White" which is the key to this kind of blending (IIRC Bill Alexander did something similar). Catch is, this is a technique than only works for oil paints, which unfortunately are unsuitable for a backdrop due to the shine that they have. I tried a sample (16x20 I think) and it was easy enough to blend, but after it dried and I held it up in my backdrop area, almost all I could see was the shine due to the angle of the layout lighting (which cannot be changed). If it were not for that, then it would be a lot easier for me to just go with the oil paints. From what I have learned, there really is no good way to get rid of the shine, you can only tone it down but still there will be some.
Have you tried applying matte varnish once the oil paint completely dried?
I though that you perhaps do not need that many different shades if you can apply a single lighter shade in coats of varying thickness.