Another thought might be around keeping your kid warm. In winter, you're going to stay warm by pedaling. You're little one won't. Winds can be pretty nasty, so I could imagine it would make a lot of sense to have a transportation option that is enclosed so that wind stays out, if needed. ...which sounds like a kids trailer option to me.
And on another note: I recently saw a kids trailer insert at MEC that is supposed to support the neck, allowing kids to start in a trailer a little bit earlier. I think it was this one:
https://www.mec.ca/en/product/5041-8...Baby-Supporter
I'm not sure if this one would work:
https://www.mec.ca/en/product/5054-0...6-2--2016-2017
Please keep me/us posted.