Is it possible to attend law school part-time and work during the day? I know that UIUC doesn't have an evening option, but several other ILL law schools do. I went to law school part-time with a wife and kids, and it's difficult, but it can be done. I still managed to graduate with a relatively high class rank, did internships, etc. You need discipline and stamina, which as a 22 year army vet I'm sure you have.
As far as paid internships, good luck. You may be able to score one, but they're few and far between. If you really need to make money, either work and attend at night or take out loans. Personally, considering the state of the job market, I'd look at the part-time option before accruing debt.
Lastly, can you obtain cheap insurance from the VA or from your wife's job? I was under the impression that teachers were eligible for family coverage at low rates. If you have any specific questions about attending law school with a family, feel free to post here or PM me.