I worked quite a lot during my first year of medical school -- about 20 hrs a week at night as a social worker at Arkansas Children's Hospital. It worked out fine. I did well in school, but I was exhausted. I decided NOT to work 2nd year. But it's doable in the first 2 years. don't think it'd be as easy in the last 2 years.
OBRN, are you planning to work then? Wouldn't you have to be at least part time? I know there is health insurance for students, don't know if that would cover families. My state also has state sponsored health insurance for kiddos. Mind if I ask how many you have? And when will you start medschool?