We get used to the way things are -- even when its not what we desire - and change is scary. I think that what's you're afraid of. Keeping the status quo has a bit of comfort to it - even though there could be something better.
I think a money management class is a great idea - especially since you already know you and Brad are not good at handling money. I'm sure part of the class would focus on how you think about money, what it does for you emotionally - that sort of stuff.
From what you've said here in your journal, it sounds to me like getting out of debt would mean LOTS of disposable money each month. You could start saving for retirement - you could buy a house more suited to your liking - you could take the kids fun places and build more family memories.
If you feel strongly that you should have that $1000 set aside - then work on that first. But make sure that you don't spend it on non-emergency type things. With your 31 parties it should only take about 3 months to get the money together. Then start putting all of the 31 commissions on bills.