Looking to replace the Shimano wheelset that came with my 2010 Cannondale Synapse. $600-$2000 depending on what my research tells me. These will move to a new frame i'm buying in the next year or two. I'm against spending less only to spend the rest of the item's lifespan wishing I'd spent more but don't want to overspend either...

I live in Denver and for the most part my rides are 60-100 miles combination of flat and steep climbs. Looking for all round wheelset. Love speed, 110lbs and hate crosswind, and don't want a super stiff ride. Thoughts? Where did you start? How did you decide?