Well, I am quite experienced in the double stroller debate, with 4 kids under 8, one on the way, and a day care, I have used my share of all kinds of strollers. Here is my personal vote. With your oldest being almost 3, I am not sure I would encourage the double stroller as your primary stroller, maybe a sit-n-stand. Although, they are not easy for the toddler to sit in, when the baby seat is strapped in because the seat has to be reclined. So, if he really likes riding in the stroller, it might be worth it for you, but at 3, mine enjoyed standing. Now, I do LOVE my side by side jogger for trips to the zoo, Six Flags, walks around out side etc, but they are not practical for shopping trips. I currently have 3 different strollers, and could not live with out one of them. I do love my quattro tour double, but mine was 15 months when the baby came along. I have the double jogger, and I still keep a single umbrella type stroller in the car for times when I may only have one child to deal with (a rare but cherished treat:) Good luck making the decision!! ~A.~