I definitely would not enlist in the Amry, guard or not, if you're looking for money.
Also, sign on bonuses really aren't worth it. Plain and simple. Usually only certain jobs qualify you for them. Also, you don't get all of it up front. Say they offer you a $15,000 sign on bonus for signing up for 6 years rather than 4. After you've been in service for 1 year, you'll get half of that bonus. $7,500 minus taxes, of course. Comes out to right around $5,200 or so probably. Then you get the rest over the remaining term of your enlistment every year. $1,500 each year BEFORE taxes.
As far as school money goes the Reserve/Guard GI Bill & Kicker(depending on your job) is nice, but you have to have the money to pay for school up front. Only once you take the class, and pass it, will they reimburse you for that class.
In the ANG I can almost gurantee you're going to deploy. Heck, I'm in the Air Force Reserves, and I've been to Iraq and Afghanistan more times than I can count.
Also, good luck trying to be a "weekend warrior." Like I said, I'm in the Reserves, and I worked a solid straight 9 months last year. Every month I was overseas at least 10 days. Hardly the '2 days a month, two weeks a year' people think it is.
I'd suggest looking into going to becoming a police officer. Most likely better pay, you'll never deploy overseas, and you'll be around your family all the time. Also in 20 years you'll receive 100% of your pay for retirement.