Do you have the WSD Pilot 2.1 or the men's version?

http://www.trekbikes.com/us/en/bikes...trek/pilot21/#

http://www.trekbikes.com/us/en/bikes...k/pilot21wsd/#

Your problems with the Trek could be related to poor fit. Whatever new bike you get, make sure it fits you well.

I don't know anything about the Specialized bikes you mention. It looks like there are many versions of the Ruby and Dolce available. Which ones are you looking at?

http://www.specialized.com/us/en/bikes/road/ruby

http://www.specialized.com/us/en/bikes/road/dolce