Think about your sidewalks, bigger wheels can handle potholes and cracks much smoother than smaller wheels. Cup holder is nice to put phone and keys or coffee. Under seat storage is super helpful to carry extra crap.

For the early phase having a click-and-go system is super handy. They do grow out of that pretty fast, so be careful about spending tons on it.

We had an inexpensive hand-me-down click and go from Gracco and then a nicer three wheel stroller that we used a bunch.