Broken

I am about to make a "make it or break it" decision. It could work out. Or it could go horribly wrong...
Right now we've upped our debt by:
$795 on parental "payday loan"
$150 on car expenses
$930.13 on Hubby's commute expenses
$200 micellaneous
=$2025.13 Total

Am I proud of this? No. Was it necessary? Yes.
I'm thinking I'm about to up it some more.

We are $1001 behind on being completely current on bills. Don't get me wrong, they always get paid. We suffer in other areas to make sure of this. I toss and turn at night thinking of it. Anyway, I have a whole system of setting portions aside for quarterly bills and splitting expenses of monthly bills across both paychecks. It's always worked for me and it's mildly complicated to look at... but anyway. We're $401 behind on setting money aside. The most worrying is $188 of that is for health insurance- one of our top expenses. The other $600 is half of our mortgage that I've been two weeks behind on for several months and end up paying $3-$6 in late fees on monthly.
My idea is to take bills that I can put on a credit card and doing so. Just to catch up. Is it really catching up if I have to pay for it later plus interest? Nope. But I don't know what else to do. I'm slightly freaking out.