Yup, the Jeep payment did jump out at me, so I'm glad to hear you're already on the path towards replacing it. Lhamo's advice on that is good.
The extra gym membership also seems really expensive to me. Unless you are *really* making great use of it on a *very* consistent basis, I would definitely cut this.
Why is your Pontiac car insurance so high? I know that rates are highly dependent on location, so it may be fair, but I would at least compare prices from a few other insurers, like Geico, Progressive, etc.
You say that your employer offers a 401(k) with matching. I would DEFINITELY make it a top priority to invest in this to take full advantage of the matching funds, at a minimum. That is totally free money that you are leaving on the table. Essentially, your employer is saying, "here is bonus money," and you're like, "nah, no thanks." I realize you've had a lot going on that has contributed to your delay in getting the 401(k) up and running, but now that things are a bit more settled, I would get this done! If you don't know much yet about investing, I would probably just pick the target date fund (like around 2050 or so).
I also think your wife's budget of $180 per month on hair and nails is excessive, but you would need to decide if that's a battle you want to fight or not.
