Wow, lots of responses very quickly!
Thank you all for the input thus far, a bit more background:
Checked on the auto insurance, and got it lowered to $90/month for both cars. Still not too sure if that's actually good or not.
Two cars- We are not in an area with public transportation, and both my wife and I are a bit uncomfortable with her and the new one not having transportation if needed. The rental car is a good idea, and we do have neighbors we could rely on in a pinch, or even selling the car with the note on it (according to KBB it's worth about $12,000 here) and getting a cheaper, older car. Not sure what the right solution is for us, but I'll take a look at those options, thanks!
Cash on hand- Honestly, that kind of got away from me. Before we decided for my wife to stay home we, I hit a work bonus as did she from her work that really boosted that, and I decided not to mess with it until after the baby was born in case any unforeseen medical expenses came up. Not exactly rationale, but there it is. I'm not sure what the best use for this cash is at the moment, obviously not what it's doing though. Thanks for lighting the fire for me to figure out what to do with that. I'm debating paying off some of the mortgage, investing, or splitting between the two. But that seems to be a common theme around these parts. I'd welcome any input with thoughts around that as the mortgage is 4.5%.
DIY haircuts- Great idea, I'll check with the wifey.
Wife side hustle- Once she is adjusted with the newborn, we have looked into babysitting for some friends of ours. I suppose it's more like daycare than babysitting, but if that works out it would be $500-$600 a month. I'll show her the leapforce as well, I have not heard of that before. Thanks for bringing that up.
College- We are planning on helping as we can- I paid for my own education and it was a good experience, but I think it would be neat to at least cover some/most of the cost for college for the kiddo.
Charity- We are actually hoping to increase that a bit. I do understand the long term cost of this, but for where the money goes, the cost of not doing this is much greater to us.
Regarding the commute- I'm scouting a place to move closer to work, it's a start-up so part of me wants to wait until it's a bit more stabilized, but that's probably just me rationalizing because I hate moving and love our home. We'll probably rent out the house and rent somewhere for a bit if I can get all the details worked out. I can telecommute occasionally, but that will not be possible starting in about a month-hopefully I'll at least have a gameplan of where to move to by then. Depending on where we move, this could actually allow us to get rid of one vehicle, which would be the goal.
I realized I did not at mobile phone plans and internet in the expenses category- those are both paid for by work.
The wife is breastfeeding, and we actually somehow ended up with enough diapers for the the kiddo from baby showers etc. that were thrown to last us until he's potty trained as far as I can tell.
My employer does not have a flexible spending plan.
I've heard about the elimination communication thing before, but I didn't know it had a name. I have family in Japan and apparently that's the normal way to potty train over there according to them. I'll check with the wife and see how she wants to do that as she will be the one with the baby most of the time.
Regarding the leftover amount each month, what would the going recommendations be on that front? I was thinking something along the lines of:
$300 to mortgage (allows us to pay it of in 15 yearsish instead of 30)
$500 to investing
$200 to college
Thoughts?
And thank you very much to everyone who has responded so far.