Motion

I had a four wheel BOB (passed it on two years ago). That thing was a beast no matter what weather. It went through sloppy or piled up snow. It was quiet and smooth. It folded quickly (important for the train/bus/ride share). It was on the heavier side to carry while folded (easy to one hand it), I am convinced that it was able to take more abuse than some of the other brands. It survived multiple flights (gate checked). The wheels were great after hundreds of miles. It was easy to clean. And it has tons of carry space. I could do a full grocery trip and pack it all on the stroller with the kid in it to walk home. I never needed to repair anything. Nothing broke or ripped over the years.

I have the BOB with addon Velcro attachments for water + junk and it's an excellent product. I'm 6 ft and I think the adjustable/tilt handle is well designed and comfortable. The adjustable sun shade for kiddo is nice with a clear plastic window to be able to check in on them periodically without breaking your stride. The thing is very well built and sturdy. It's definitely a "buy it for life" quality product that you should be able to pass on to someone else after your family has outgrown it. My only issue with it is that when it's folded down it still takes a lot of space in your car. We have left it at home every time we went camping because trunk space is more important.

It's going to depend so much on how and where you plan to use the stroller, and whether you want something that can eventually be used for a second baby. I don't drive and we knew we wanted 2 kids, so I needed strollers that really worked well and had okay storage capacity. I went through a few different strollers to accommodate different activities and different life stages. All of them were used in conjunction with babywearing because sometimes in the city a stroller just doesn't work at all. I got a City Select first because I wanted something I could convert when we had a second, and the versatility was nice, but all the front to back strollers are so unwieldy to push. Having a tiny baby facing me (preferably not in a car seat) was important to me, and it was a good choice for that, but once both kids were bigger I sold it. I also had a not-quite-umbrella stroller, the Zoe that isn't the super tiny travel size, for those days I wanted to keep it light and only needed it for one kid, but they're really only well suited to smooth floors, like museums, so I only used it if I really needed something small and easy to fold. My second set of strollers, once I knew we weren't gonna have anymore newborns, were a City Mini GT and a Mountain Buggy Duet. The GT is a really solid choice as long as your kid is old enough that you feel comfortable not having eyes on them at all times. Sturdy, handles well, basket is not amazing but it's good enough, folds quickly, and they're popular enough that it's easy to find one used - I think mine was $20 on craigslist and all I had to do was stuff a little piece of cardboard into a spot where the front wheel liked to stick. The Mountain Buggy Duet is relatively unknown but my absolute favorite for when I needed both kids in a stroller. Rugged as hell, smooth to push even with one hand, amazingly shockingly astoundingly narrow for a side by side - I think there's less than an inch difference between it and the City Select single. You can fit this thing on a CTA bus without folding it or blocking the aisle (I did avoid crowded buses with strollers but I surprised a lot of people when they saw it squeeze in). You can take one seat off and attach a shopping basket if you've got one in preschool all day and the other at home with you running errands then put the second seat back in for a weekend zoo trip. It was a pain to fold but I rarely needed to fold it. It's not the best stroller for big kids since it's so narrow, but my oldest was a shrimpy toddler. God, I miss that stroller. If I knew then what I know now I probably would have gotten it and just used it with the basket when my first was born. I also borrowed a Bob double to get the kids to and from school when we were avoiding the bus during covid and it snowed and snowed and snowed and snowed one winter. It did well in the snow but it's so so big, I couldn't even get it in my garage without folding it. If you plan to do a lot of trail walking off road kinds of stuff, a single Bob would be a great choice once baby is big enough, but I wouldn't bother for just city walking.

The 3-wheel strollers are great for tall kiddos. If you can find a single bob, Thule, or guava for your kiddo on marketplace I’d pick it up, or you can rent one. Renting is harder if you’re not staying for a longer trip. You could also just rent a double from the park so he has someplace to sit. He’ll fit in a double, it just won’t be super comfortable, but it’ll give him a place to rest.

We have a bob and I LOVE IT. I use it almost every day. Pricey but worth it imo Edit— sorry, I didn’t answer any of your questions! Our bob is a side by side, it fits thru standard doorways so I’ve taken it into lots of stores and dr offices. It is heavy but I can manage it on my own still. I love its off-road capabilities. I take it on hikes (not too steep). I also got a single bob off of fb marketplace bc I loved the double so much. It’s nice to still have e a single stroller too. The basket underneath seems roomy to me. It fits a large pizza box. It can carry all of our stuff. You’ll have trouble shoving a bulky diaper bag in there but I’m sure you could manage if needed. I’ve used it as a grocery cart when my kids were v little. You can get a snack tray that snaps on.