Chariot Sport single

We did a double Thule sport chariot. Sling for newborn. It was good for around town and totally bomb proof with a jogger wheel in the winter. Total nightmare to get into a vehicle though.

For the stroller, I spent about $2000 on a Thule chariot sport (including accessories) because I was training for an ultra-marathon when my oldest was a baby. I've hauled it up mountains, and pulled it behind my bike for hundreds of kilometers. No regrets on that purchase, but for the stroller that I push through the grocery store, and around the block with the dog, I use the cheapest one I can find that the car seat drops into (a Graco). Both strollers are just right for their use cases, and I don't see a lot of use for a stroller that occupies a middle ground between the two, but your usage patterns may differ.

What a good question. For me, lying flat/newborn compatibility, and the amount of space it took up in the car trumped all other factors in the end. We had a secondhand baby jogger and it was just TOO BIG. Carseat compatibility is like negative important in my mind, and totally irrelevant if you have a lie-flat stroller or bassinet. My kiddo basically stopped wanting to be in a stroller as soon as she could walk at 10 months so now the stroller is a glorified bag/luggage cart and I'm so happy I didn't get sucked into snack trays, reversible seats, suspension, baskets, wheels. We ended up with an Ergobaby Metro+. I will add we also have Thule Chariot single that we use walking in the snow and on the ice. I was hellbent on being a one stroller household but I don't mind this because it's also for biking and will outlive our stroller by a lot. But unless you really live in the country I don't think it's a reasonable sole stroller.

And yes, as other have mentioned: a running stroller (we have the Thule Chariot).

Tandem for the win (I have the gazelle and it is the workhorse). Side by side doesn't really work in an urban city. It is more like a FU to pedestrians on the sidewalk as you literally block it.  I also have a Thule chariot and veer which takes up as much space as a side by side. Maybe the wagon XL is a tiny bit more narrower. It is unwieldy to navigate and good luck if you go to small shops because you can't navigate through the aisles.