Hellobee Boards

I actually found it to be ok pretty much right away. DS is 3 and DD is 9 weeks. We don't have a car though, so I use the stroller with a wheel board.

Geez, I don't think I could have handled both very well during winter, at least when LO #2 was new. I nursed before I left the house and baby wore while we were out so my hands were free with my toddler and it worked out well. By the time my LO was 8-10 weeks, I felt good about going out with both.

DS was 15 months old when my daughter was born. I got out by myself at about 3 weeks(after all my help went back to work). I couldn't be cooped up inside. It's horrible in winter since I still have to keep close tabs on my son(now 21 months), since likes to run.
They probably started going more smoothly once dd was about 2-3 months old.

@Maysprout: I still used a stroller for my older kiddo, so I unloaded our gear in the basket. With my youngest, I put her in the Beco Gemini, it crossed over by back to give enough support to lift LO #1 into a shopping cart or to put him in the car, put the stroller away, etc.

@Maysprout: I used my Beco a lot with the baby, I'd even use it with the toddler. I have a double stroller, but DS doesn't mind being in it.

I confess I've been rather wimpy about this. I can't count on my 2-year-old to not run or have a tantrum, and there's always the chance baby will need to nurse, etc. I will go certain places like the park or music class or the library that it's easier to wrangle both. But I avoid the mall, grocery etc if I can help it.

@Maysprout: adding a pic of our setup with the wheel board. We've only had a little bit of ice this winter, so it hasn't been too bad using the stroller. So far I haven't worn DD very much because I feel like she stays warmer in the stroller.