Bugaboo - Donkey 6

I'd get Donkey but leave in US. Too bulky for cabs with luggage, could get damaged in checking. So you are getting them seats on the plane? I'd prefer Doona X because the Urbn flex is bigger and you'll need 2 and they can recline more, and people in dense cities usually prefer taking a Doona out in a taxi than the stroller system (and definitely not 2 pipas and a donkey frame) but either seems fine. In the US they'll usually do a car seat test if a baby is super small (like maybe under 6 lbs). Planning to baby wear (not in car but in transit) might be helpful.

I think you have a bias problem with “…that have one baby in the front and one kind of neglected in the back…”. For the first year, that set up is awesome - and keep in mind - infants can’t see that far or that well yet for a bit - so the view isn’t a concern. We had the city select double with a conversion for peg perego infant carriers and it was awesome. We also had a double bob and a bugaboo donkey (side by side) and two singles. For the first year - the city select was it. We never, ever had concerns about one baby being neglected. You can easily see both and both kids can easily see around. I would revisit the stacking single file double stroller.

I would suggest going to a big department store where you can try different models and see how it feels. Online reviews are nice but seeing it irl is really useful. We got this tip at a baby expo, we obviously looked overwhelmed. We saw the side by side Donkey and it felt SO wide. The tandem Vista felt much more manageable, that's what we ultimately bought and we're happy with it. They are very expensive new, but hopefully you can find places like FB Marketplace that has reliable second hand items. Short of car seats, most of our newborn items were hand me downs. I drove 2 hours to buy our Vista, but it cost $550 (and it came with all the accessories)while a new one was $1k.

I absolutely loved the Bumbleride Era I had with my first. You don’t need a bassinet attachment because the seat itself can lie flat and serve as the bassinet (I think there is an ever so slight incline, but it’s barely noticeable and it honestly made me feel better post feeds and while going downhill). It was such an amazing stroller, so smooth on all terrains (sidewalks of MA, some trails, etc.) I ended up having Irish twins and had to switch to double stroller and got the Bugaboo donkey with bassinet attachment and definitely miss my bumbleride constantly!!! We had a universal carseat adapter for the Era that could fit with our Clek car seat but honestly didn’t use it more than twice

Bugaboo donkey can be single or double!! Side by side is the way to go. Tandem gets so heavy and hard to maneuver when loaded with 2 kids

You should be able to find something. Here in Germany, I have seen a lot of Bugaboo Donkeys listed secondhand for around €500, and Foxes for around €300, often with tons of free extra accessories  I just bought a Bugaboo Cameleon 3 for €90 (including extra accessories). That means it’s an older model, of course, but it still works great.

We have the bugaboo donkey duo. I live in a major city and do not have a car so having a stroller with ample undercarriage storage for groceries and has the capacity to have our kids in longer was important. Not to mention the ride is smoother and much easier to handle on bumpy sidewalks. I’ve used a bunch of other strollers when I was a nanny and this one truly is the best stroller I have ever handled. The stroller also can hold kids up to 50lbs per seat and we have 2 under 2 rn and plan to have more kids in the future once we move out of the city so we felt like it was worth the cost.

Honestly the bugaboo donkey is THE best. Almost everyone uses it where I live, I have had 3 strollers and the bugaboo is the best one. Look at Facebook marketplace I got mine for $200 off there. It is also worth the price as it can last YEARS

Bugaboo Donkey is very wide, look for something that not so wide, like out n about.. we have that; much more narrow; a dream to push and easy to close! With tandem, even if you are ok with it, as they grow your twins might fight as to who should get the better view and refuse to get in; I have heard that happening, so chose side by side!

We went with bugaboo donkey side by side but had the same dilemma - it IS big, but when you have twins you are a travelling circus regardless of size. We love/loved it overall great stroller. We still use it regularly and my twins are almost 3. It fit through most doorways as it’s the size of a wheelchair, but when they were small I would actually often strap one to me and use the donkey in single mode (which is actually smaller than most single tandem) which I loved for grocery shopping. I should note I live in a city so we are walking everywhere - I think if driving everywhere a side by side when kids are bigger - a stroller that has a one handed fold (Zoe, valco, jeep) would be wise to look into for getting in and out of the car. My only complaint with donkey is getting in and out of the car/folding it up isn’t fun, we kept ours set up and just plopped the babies in. For reference we also have an umbrella double travel stroller for flights, and a bob double for running. Donkey is my fave but all for diff purposes!