Hellobee Boards

@Littlebit7: I'm in a very similar situation without the snow. Everyone I talked to said to wear the baby for the first few months and by then the older one might not not even need a stroller. I'll let you know how that goes...im already overdue so #2 better show up soon!

We have a Joovy Caboose Ultralight (https://www.amazon.com/dp/B01BMAW0M2/.) It works perfectly for us - it's super adaptable, so it can fit most infant carseats while they're still in the bucket seat, and it also has a built on standing platform and seat on the back for the older kid. Can't recommend it enough!

I agree with PPs to just babywear in the winter and keep your current stroller.

But then you have some options--

1)keep your stroller and get the buggy board.
2) get a narrow side-by-side like the Mountain Buggy Duet
3) get a more compact double inline, like the Britax B-ready
3) get a sit-and-stand type of stroller. We just got a Chicco Bravo for 2

We had a Britax B-Ready (still have it actually) and it was really great for the first 1.5 years that we had both girls. We bought it before LO1 was born. It has so many configurations and is really versatile, but is more compact than the City Select inline stroller, so it's easier to get over curbs. You can also fold it with both seats attached. You can click in an infant car seat, a bassinett--it can be a single stroller or a double. And the car seat can go on top or bottom (with an adaptor). But our top seat broke on one hinge (where the footrest can be adjusted up or down) and it costs $140 to get a new top seat, so instead we just got a whole new stroller (the Bravo for 2). The push on the Britax was actually better, but the Bravo for 2 is lighter, so it's kind of a trade-off.

Most of my friends with two kids have a side-by-side, but I just don't like how wide they are.

We bought a buggy board (the Lascal one) for our Quinny stroller. Our DD is almost 4 and loves it. We didn't buy it until the baby was 6 months old and started riding in the stroller. Over the winter I wore him if we were all out together but my DD was in daycare so most of the time she wasn't with me and the baby. Now that the weather is nice and we walk a lot, I'm so glad that we got the buggy board.

@Littlebit7: just a note about the Vista as a double in the snow- impossible. When my second was born the older one was almost 2.5, and she had to sit in the rumble seat in the front. I could barely push her over the tiniest bit of snow. I'm sure newer options are better (this was the old Vista) but if you will be walking in the snow I would guess any front to back double like that could be hard.

I think a ride on board on a goodsolid single sounds good

What about pushing the youngest in the stroller and wearing the big kid? Or what worked for us was to have our oldest tide her bike (admittedly we don't get snow but that kid could bike for miles!)