I was a nanny before having my own DC and have used every single stroller under the sun.
When we picked ours we took in consideration all the "test driving" I've done plus our life style.
We lived in the city but owned a car and drove a lot to friends' houses and travel.
We ended up with the Uppababy Vista for the first 2 years and never needed another stroller.
It did beautiful during the newborn stage - we never used the carseat adapter, I'm not a fan of babies in carseats when they're not in the car. We always used the bassinet. It was AWESOME! It even worked as a travel bed for the first 6 months so we never had to use the pack 'n play.
The basket is HUGE! We did all our grocery shopping walking and never needed anything else to carry our stuff. When traveling the basket was very handy, all our carry on fitted there so we didn't need to worry about luggage and the stroller.
It folds relatively easy (gotta practice a little) but the stroller fits anywhere, including the XRay machine in the airport
We did snow, sand, pebbles, grass, bumpy sidewalks... I called it my little jeep.
DH is tall and I'm short. We both had problems when trying other strollers with kicking the axle in the back... him because of his long lets, me because my short arms. The Vista was perfect for both of us!
Obviously we got nasty looks at the metro but I could not care less. It fits perfectly where strollers are supposed to go - the elevator and the spot for wheelchairs. I always made sure I was at the very end or very beginning of the platform so we never disturbed anybody.