Caboose RS Sit & Stand Double Stroller

4 in total, with two children. I don't drive and we walk daily, in all weather. I had a Graco Comfy Cruiser as my daily driver. Less than $200 and it was an absolute workhorse. I used it for over 6 years, between the two kids. Huge basket was perfect for grocery shopping. We also had a Joovy Caboose, for the short period of time when my older child was not a reliable distance walker, and needed a place to rest. And then two running strollers - a Chariot Cougar 1 and Cougar 2 (single and double versions of the same stroller). My youngest is 4 and we are still using the Cougar 1 for runs together.

In-line is so much easier.

Depends on how old your first is. I have a joovy sit and stand that’s good if your oldest will be 2.5-3+ when baby is born. Younger, I’d get a full double. Or, just be a cool mom and get a wagon. Wagons are the same size (usually) as a double stroller front to back but way more useable space. I have a larktale caravan for my two and it’s amazing. It even has a car seat adaptor for newborn days.

Having maneuvered both, trust me that the in-line strollers are worse. The number of ankles that would be clipped because it is so hard to gauge depth… Side by side is wide but much easier to control your footprint.

My older kid had one really good tantrum when she realized she had to walk and then she was fine after that. We ended up getting a secondhand Joovy Caboose that we really like for neighborhood walks, but otherwise my older kid just walks.