I agree with mfg's answer; most of these are convention and there are no good rules. However I wanted to add that in some cases you can eliminate certain combinations that don't make as much sense.
highly sophisticated
In this case things that are more sophisticated are often seen as better or more "advanced" and thus "higher" than the base, simple, unsophisticated things. It makes sense to "order" the sophistication from high to low.
extremely sophisticated
I think this is a perfectly acceptable way of expressing the thought.
highly happy
In this case I would say happiness is not ordered and more emotion is not necessarily better than less. However this is not a hard and fast rule, more of a guideline (the phrase highly happy might sound a bit odd to me, but I probably wouldn't consider it a mistake).
So I think you have a fairly high level of freedom to choose your modifiers, and as long as you don't pick one that is really inappropriate, people will understand you, and probably won't think anything worse than "This person is from out of town".