The answer is often found in the question:
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how can Google calculate a quality score for a keyword if I have 4 different ads showing for it going to different landing pages that are optimized for the a better conversion rate for the ad not the keyword.
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It kind of doesn't make sense to have a single ad group for 4 completely different landing pages. With different I mean,.. 4 different subjects and not 4 different pages that have the same subject. (which you could use for testing different landing pages).
The quality score is more related to the relation between keyword, ad(s) and landing page(s) than to just ad-landing page relation. I'm now just guessing, but it would make sense if Google would base the quality score on the lowest possible value.