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

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Got a Vista stroller second hand before baby came because of the wheels and bassinet. However, we have a small Mazda cx-3 and the Vista is huge. It can sorta fit in the trunk but the wheels hit the ceiling of our car and it feels slightly too close to the baby seat, as it sticks out. Once kiddo is bigger we'll get a tiny umbrella stroller. I will say, the Vista is so comfortable to walk (mostly road and compressed gravel for us) but didn't do very well in our snow this year. Was hard to push in our long snowy driveway. Got the Thule cheetah and it's also too big to fit in our trunk unless we bring back seat down ... So, all I'll say is that having a small car makes a huge difference and if you can find a happy medium with a comfortable small stroller you'll likely only need one. I almost never bring the strollers anywhere and use a baby carrier simply due to car size and foldability.
We have an UPPAbaby Vista - works well with two bassinets, car seats, or stroller seats. We even get our four year old to stand on the bar running across the middle so we get three kids on there. It’s expensive but it’s been a workhorse for 4.5 years now and held up to much abuse. We also have a Thule side by side jogging stroller and the four year old will sit on the front between and ahead of the twins. That’s getting tougher to steer with so much weight out over the front wheel but it’s nice for neighborhood walks to the park.
We have the same age gap and our youngest is now 5 months. We primarily bicycle (e cargo bike) or walk everywhere with a bit of public transport and even more rarely drive. We have all of the set ups: single travel pram/buggy (YoYo), single running buggy or double bike trailer in stroller mode (both Thule) and a Bugaboo Donkey with the option to do single with ride on board or side by side double. Up until recently we primarily got around baby wearing our littlest and 3 yo walked. That’s my preference for quick outings or if my wife is with us. When I’m solo with our girls I like having the Donkey and let my eldest decide if she wants to ride in it as a double, single, or just walk. Even in single mode it’s very quick to swap from baby mode to toddler mode once they’re out of the bassinet and in the standard seat. I like the double for if I’m planning to let baby nap in the buggy as it’s nice to have the option for big sis to have a ride without waking her. I also really like it for the rain, we’re in England so it’s wet a lot and I love being able to have them both dry in the buggy on days it’s really pissing it down without spending an age getting them dressed up in waterproofs just to pop down the shops. And I still like the buggy option for my 3 yo as we often have v long walks as a family that avoids cars.
Pushed all the wagons including a veer.. Thule is the way to go
Depending on the type of trails you’re running, the Thule Chariot can work well. Your pace will slow, but it can get over some pretty big bumps and fits on most single track
I used it until they were about 8/9 months. Laying down until 7 months (premature babies), sitting for the last two months. Face forward, cause they loved people watching! Rented the thing. Now I have a Thule bike car that is also a stroller (ideal because we don't have a car, annoying because it doesn't fit through the front door).

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