Well, I decided to test the waters and talk to a few dealers.
They are definitely dealing on these vehicles with the new updated 2016 models approaching. We ultimately decided to keep what we have, because a car payment while raising a child with mom at home and only one income doesn't feel like a good idea for us.
When we bought or house, I was completely confident signing a mortgage for far more than a ~$20,000 minivan. I know it was the right thing to do for my family. Thinking about a car payment had my hands shaking and my stomach in knots.
I think if I'm not feeling good about doing this, then it's not the best thing to do right now. It would push us back considerably on our goal of paying our 30 year mortgage in 15 years. The way I see it, I can stretch myself to buy the most base model vehicle now, or I can comfortably afford something far nicer in the future.
The cars are cramped now, but our son won't be in the carseat and stroller forever, and I think we'll be better off in the long run by sticking with what we have.
I really appreciate all the input, one of the reasons I love this forum.