I lived in Beacon Hill with a baby and no car, and this was before getting things delivered was much less of a thing. Overall, it was totally fine. I generally walked everywhere anyway, so it wasn't a big deal. We did have to plan things a little better, just so we weren't dealing with that T at rush hour. Shopping usually meant going more often and getting less stuff if I had the stroller with me. Bigger stuff would have to be delivered or picked up with a ZipCar.

We "invested" in a Bugaboo stroller, and it was totally worth it despite the cost. It was super maneuverable and easy to push around. It also folded and unfolded quickly and easily, so getting around in places with stairs wasn't too bad.