
Joolz
Aer+
Travel-friendly, city-nimble, but tiny storage and struggles off-pavement.

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Bugaboo kangaroo for large stroller with incredible wheels (for these sidewalks and streets and cobblestones). Uppababy Minu v3 for travel stroller in the car (also fits in the carry-on compartment of airplanes), and for smooth ground (going to a mall? American Dream?)
Bugaboo Kangaroo fits this description. The wheels are powerful and can take on snow and rough terrain. A bassinet that converts to a stroller seat is included with the stroller, as do adaptors for car seats. When the time comes you would need to purchase a sibling seat, and/or a wheeled board for toddlers and older children if they prefer to stand while being carted around.
I have the bugaboo kangaroo and love it but nice list!
I love my Bugaboo strollers. However, if you need it to be smoother on rougher terrain, I’d get the Kangaroo or a used older full size model. I also have the butterfly and while it’s great to have in tighter spaces, it’s really better when they’re older or you use the car seat attachment. My ride or die is my old Chameleon. She’s taken a beating with two kids and is still rolling smooth and strong
I wouldn’t spend a lot on baby furniture. They don’t use it for very long. Maybe one nice dresser they can use until they grow up. Expensive cribs, etc are temporary and don’t perform any different than cheaper cribs. I’d also consider convertible car seats that have a larger height/weight limit thresholds (if you both have cars). I wouldn’t spend a ton on the infant seat either, you may have a baby who hates it early (mine did!). I’ll say my Bugaboo stroller has been worth its weight in gold. It handles like a dream and we hauled it everywhere. I’d also do bad things for a night nurse at the moment, my 2 week old is giving me the business from 1-4am and I am TIRED.
Not on your list but I have the bugaboo kangaroo and love it. I did lots of research and comparisons and ultimately found an open box deal on one. I have no regrets! It’s easy to maneuver, take apart and store, high quality materials. And converts to hold 2 children if you plan to have another!
We got the kangaroo and we fricken love it.

Joolz
Aer+
Travel-friendly, city-nimble, but tiny storage and struggles off-pavement.

Bugaboo
Butterfly Series
Durable, compact for city travel, good storage, but expensive.

UPPAbaby
Cruz V2 Stroller
Durable workhorse with massive storage, but heavy and bulky.

UPPAbaby
Minu V3 Stroller
Compact travel, decent storage, but pricey, seat not upright.

UPPAbaby
Cruz V3
Durable, massive storage, great service, but heavy and bulky.

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Joolz - Aer+

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UPPAbaby - Vista V2

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Thule - Urban Glide 3 Series

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Bumbleride - Era

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Joolz - Aer+

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Thule - Urban Glide 3 Series