Thank you both for the responses.
I'm in Chicago - will definitely check out Four Star and you are correct, I have not test rode any of these yet. Four Star's website is awesome and they look to have a ton of options, so I might just head up there this weekend and chat with them, hopefully they have some of these bikes in stock for me to look at.
My concern with riding on city streets is less about the physical dimensions, and more about just handling the weight of a cargo bike (with kid) and maneuvering slow speed at intersections, stop signs, etc in tight bike lanes and/or between vehicles. Our bike infrastructure in Chicago leaves a lot to be desired and being able to dodge opening doors and stop quickly, as well as squeezing between lines of stopped cars are all useful capabilities. These situations strike me as more challenging on a front-box style cargo bike, but maybe that is a non-issue.
I actually saw another parent at my daughter's school riding a Bullitt earlier this week and briefly chatted with him about it. I have seen bike messengers on these bikes before but never really dawned on me that they could be equipped to carry kids. His had a plastic box that his kid rode in, but I see on the Larry vs Harry website they also make a seat accessory, rain cape, etc. The box actually looks more fun for kids to ride in, even though I'm sure the seat is way more comfortable.
Thank you!