As much as I wanted someone to just tell me the 'perfect' stroller, everyone was right in saying we need to decide what we wanted/needed and try them out. That became my obsession this last weekend with a number of store visits & tons of internet reading & video watching.
We've decided to go with the Britax B-Agile http://www.britax.ca/strollers/b-agile. It has bigger wheels than a typical stroller, which is good for our winter sidewalks, but not huge air filled tires which would take up too much space in our small car trunk. We also liked the Baby Jogger City Mini, but both of us noticed we were kicking the metal bar between the rear tires. Plus the B-Agile clicks together when folded more easily and stands up when folded. Also, the videos on the company website were super helpful in understanding how it works without having to rely on absent or pushy store salespeople. As a newer product (I think it first came out for 2011), we don't expect to find one second hand.
We will also buy a cheapier umbrella second hand.