Given the opportunity to choose a box in person, I typically prioritize aroma and wrapper quality/consistency. If those are equal between boxes, I usually pick the darker shade wrapper (Colorado or Colorado Maduro) simply because in my experience those are rarer when it comes to Cubans. As a result they typically offer a less common flavor profile which is nice to have in the collection.
To me, the Cuban Colorado Maduro wrapper imparts a deliciously rich and deep chocolatey prune flavor. I absolutely love this flavor, but it can dominate the blend and render the cigar less complex.
For example I have two boxes of GLE ABR 20 Trinidad Fundadores: one claro and one colorado/colorado maduro. Each has some rosado like @karp mentioned. They smoke so differently! The claro box is very fine, subtle, complex, and invites slow smoking and appreciation for the classiness of the cigar. The colorado box is less complex but just full-on scrumptious. I'm sure we can all relate to taking the first bite of a really delicious chocolate cake or mousse and then, "poof!", next thing you know the whole thing is gone and you are riding that sugar high. That's how the colorado box smokes. Just a fat punch of hedonism.
Really different experiences and appropriate for different occasions. The 40 ring gauge of the Trinidad Fundadores makes it easier to notice how much the wrapper affects the overall flavor profile of the cigar because in such a thin ring gauge, the wrapper is making up a relatively high percentage of the total blend.
It seems Habanos generally opts for Colorado Claro wrappers (do others agree?). That choice would make sense to me because Colorado Claro theoretically offers a light enough profile for the complexity of the blend to shine (coming from the claro side), while still offering a bit of the chocolatey taste we love (coming from the Colorado side). A nice middle ground for most blends.