You all will have enough to live comfortably, do the math seriously, ask your parents. Just because you purchase a 500,000+ dollar house doesn't mean you need to make 500,000 a year to pay it off? Honestly, have any of you consulted your parents about this? If you budget, live within your means and income of 300,000-400,000+ should do you just fine. And you'll still have a few million to retire on, if you budget accordingly. Come-on, if someone making 40,000-65,000 a year can afford a 250,000 house/mortgage--you can too! Trust me!
Boarding/private school maybe, again; chose one within your means. Malpractice depends on your specialty, but you can still live quite well despite it. Home/Car + insurance are something everyone must pay, make peace with-it and move one.
Remember, you'll have the majority of investments (house/car/loans) paid off by then, and with that salary you can retire with 3 million+ easily.
However, if your in-it for the money, as I've always maintained; medicine is not the field for you, for corporate law, malpractice law perhaps is best?
For me, I will plan to reinvest my skills, and money into my community-- a lot of people will be sacrificing to get me where I'm going, and I need to return that debt. I'm thinking of practicing for a number of years abroad, where I'll probably command a tenth (if I'm lucky) of what I could make in the US, and surprise, I won't be starving! Infact, I'll be living a great deal better than the majority of the population, here and there.
Average income for Americans is about 44,000 (now), with between 12-14% living below the poverty leval.
http://www.census.gov/Press-Release/www/releases/archives/income_wealth/002484.html