I have a similar age gap.
I have two prams - bugaboo bee for when I'm just out with one and baby jogger city mini double when with both. I also don't like the prams where one child is underneath the other. I tried the baby jogger city select but it felt too long in front for me. I have no problems fitting anywhere and it handles really well.
I've also got a skate board for the bee so when DS 1 gets a bit older we can also use that.
I got the 2011 model for $695.
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