You said you're definitely keeping the signature Carly and pool stuff set right? So the only other sets up for debate were the numbered ones?
I LOVE the pool stuff, so good job you for deciding to keep them. They're gorgeous!!
I would keep either #2 or #4. #4 has my primary vote though. I have an ergo tote myself (the large vintage leather one..not the Maude, the other one) and I love it. It's super comfortable so if you're a mother you shouldn't have any problems lugging it around. Plus, you can fit a lot into it and it's chic looking (to me anyway).