I agree with the OP wrote:
my wife and I live in Chicago and make $210,000/year. We had about $160k in savings as of last month.
We're 29 years old with a baby on the way. Meaning she will stop working when the baby comes. I make approximately $150,000/year.
We just bought a $500k house. Our expenses:
Mortgage/Taxes = $2,500
Cars (2) = $600/mo
Insurance = $200
Health Clubs = $200
Student Loans = $300
Gas/Electric = $100
Cable = $100
So we're at $4,000 in expenses right off the bat. Then take into account food and basic living expenses. Thats another $1,000 at least.
So our $150,000 doesnt go nearly as far as most people think. We went from having a lot of money (saving about $6k-$7k per month) to basically being paycheck to paycheck.
So, you're in the same boat as the OP of not being able to manage your money. You over-extended your expenses to the point where both you and your wife has to work to keep up with your living standard. What the hell did you think would happen when you had kids?
I mean, your expenses are so silly that you're probably going to go in more debt. Health club that's $200/month? You only estimated $100/month of electricity for $500,000 home?
How do you make that much money and have to finance for 2 cars that you bought around $19,000 each?(if it's around 5 year loan)