Stink's Chase bank will not let me put in an amount other than PAID IN FULL or MINIMUM as far as being on auto payment. So I guess what I will do is after I have seen that they have pinged our checking account automatically for the minimum payment, that will just be my reminder to go to their website and 'manually' send then another 40 or 50 bucks. Any other ideas about this?
The poster above referenced this, but just to make sure you entirely understand: Most banks will let you set up an autobill pay through their site. You could schedule a monthly payment to the Chase card for the amount you want to pay. Your bank would then draw that amount from the account on the designated date each month and send it to the card company via electronic transfer or paper check--depending on how your banks is set up.
Concerning your taxes, you seem like an educated guy. I would encourage you to do a little reading about them. Also, there's a lot of really valuable tools like "tax calculators" on the net that you could use to approximate the amount of taxes that you and your wife will pay on her additional $1000ish of income each month.
The only thought I had on your plan (which, bravo! is a huge step) was that it LOOKED like you were saying that food and medical expenses would come out of your wife's potential $1000 of income. I'm wondering how practical that assumption is and if it doesn't set you up to fall off the band wagon. I mean, yes, you may have months when you don't end up with any significant medical expenses, but food? As your wife can't currently run her day care out of the house, is there any plannable minimum amount she will earn every month? Because, even in the best of months, you and the family at least have to eat. What does that cost you in an average month? Is it realistic that your wife will earn this amount every month? If it is, awesome. If not, I might revisit the plan to add in a "food" line item, even if it drags the process out a little longer.