My twins spent several hours in their stroller (bugaboo donkey) on many days, back when they were toddlers (a lot of that time being spent having their afternoon nap in the stroller). Living in Sydney Australia. Similar car-centric problems to most US cities. But I guess we're lucky to live walking distance from parks, supermarkets, childcare centres (and now school), and a train station. And the stroller fitted folded-up in the boot (aka trunk) of our (small hatchback!) car. And our train station (and our most common destination stations) has a lift (aka elevator - Sydney has successfully been rolling out a project [1] to install lifts in more and more of its ageing train stations over the past decade). I couldn't imagine having managed, back then, without a 2-toddler stroller.

[1] https://www.transport.nsw.gov.au/projects/transport-access-p...