My oldest was 3 1/2 when the baby was born and I wish I had a Joovy from the day he was born. I did not get the double stroller at first b/c my oldest barely used at stroller after 3 yrs old. We got it when the baby was about 8 months old although much of the time our oldest could walk, there were many times that he got tired or we just wanted to move along faster and the Joovy is perfect for that. The "baby' is almost 2 now and my oldest is 5 and we still use it all the time. He loves the fact that he can hop on and off easily and can sit down for a break or stand up and look out. I ask him now whether he wants me to bring the double stroller to the Zoo, the Mall, etc and he almost always says yes.
The newer model of the Joovy comes with a thing that will hold two cups and a small pocket - it is not ideal but it works fine for us. We got the model which is lighter than the older model and I think that makes a difference for me, as far as getting it in and out of the car. Good luck with your decision and congratulations on the pregnancy!