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I live in the city, we put a combined 12k miles on our cars a year. Kid goes in the middle, dog goes beside and sometimes over him. Stroller folds small enough that it could go behind my wife's seat if we just went nuts at the store or were taking a road trip.
A second kid would certainly stretch things, especially if we were dealing with two rear facing seats as there's no way I'd get one behind me. The funny thing is that a Honda Fit actually works great with two car seats. I'd likely do that for my car (I drop off at daycare) if it did come to two kids.
And for hauling stuff from stores, I tend to do that alone, or have it delivered. If I really went nuts on the DIY thing, I'd rent a pickup for the day. Better to have a car that fits our needs for 364 days a year than drag around something we only utilize once a year just in case.
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