I agree with the 1st half of this.
The reality is that most people on these boards probably make under $30k a year. So it's hard for them to hear someone making $250k complaining. But they fail to realize that it's not a single person making $250k with no dependents. It sounds like he has multiple dependents.
Let's say the OP lives in an affluent suburb of Chicago. Let's take Wilmette, IL
Salary = $250,000
Less Taxes = $190,000 = approx $15,000/mo
Mortgage = $3,000/mo (very low for a nice area, assume he's been there for 15+ years)
Taxes = $2,000/mo
Utilities = $500/mo
Assessments = $250/mo
Car Payments = $1,000
Car Insurance = $250/mo
Health Insurance = $500/mo
Those are the basics. So almost $8,000 right off the bat out the door each month. Leaves him $7,000 or $84,000/year for everything else.
Let's go cheap and say for that whole family they only spend $1,000/mo on food. Down to $72,000 for the whole year.
Let's say he has $5,000 yearly in problems with his home (leaky roof, flooded basement, etc)
Down to $69,000
He already said he has not 1, but 2 college educations he's paying for. An out-of-state college education costs roughly $30,000/year with room and board. He's now down to $9,000 total.
Let's say he has a son in HS as well. A private HS in that area is $12,000/year.
He's now at -$3,000 for the year....
Again, I know he CAN live somewhere else and DOESN'T have to pay his kids education, but he CHOOSES to do this. And because he wants to live in a great area, and help his family out, his $250k a year income is NOT that much.
As you can see money can go VERY quickly.
As I originally said, I make $150k a year and have a wife and a baby on the way. And these #'s scare the crap out of me. I don't think we'll ever be 'comfortable' with how much money we make. The American dream has pretty much gone out the window. I don't know anyone that makes $350k+ a year anymore. Times they are a changing.