We live on the second floor with no elevator and our garage is ~50 feet from the front door of our building. (Which of course seemed like NBD when we bought the place and didn't know we'd be having twins!)
Currently when we leave for car trips I take our Joovy down to the lobby and then carry down the babies in their infant car seats and off we go to the garage. When we go for walks I wear one of them and carry the other.
I'm trying to plan ahead for when they outgrow the infant seats. It's the midwest, so in winter I'll be wearing a big coat and am not sure how wearing a baby will work with that- and am also concerned about slipping while carrying them both if it's icy.
Our regular stroller is a Bumbleride, which doesn't fit great through our buildings front door and we don't really have the space to store it in our condo- and I'm also not enthusiastic about carrying it up and down our stairs. It's kept in our garage. I'm thinking the easiest thing might be to get an umbrella stroller that I can easily bring up and down like I currently do with the joovy. It might not be great in the snow but I'm hoping that most of the time our sidewalks will be shoveled enough that we can make it to the garage.
Do you see any other options? Would you want something sturdier than an umbrella stroller but not as bulky as the Bumbleride for this? Most places we go- the Y, PT appointments, the library- I can use the Bumbleride and that had been my plan.
Added: Moving and hibernation are not viable alternatives although I have strongly considered the second.

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Re: Do you see another solution to our transportation setup?