I think the "looks for wins" attribute is just a desireable trait period (like "tries to write good code"), but the ability to weigh trade offs comes with experience and changes how one looks for wins.

In the end, you're making a smart vs. wise distinction, and the two are neither independent nor opposed.

Perhaps fixes the problem in front of them vs. thinks about the problem in context (with the context getting bigger and hairier with more experience).