math phobia vs sheer stubborn determination

We're getting a flavor for how to compare our budget to our actual spending. It involves new habits - like taking a hard look at what we actually spent (gas costs were $450 last month) and adjusting the budget to reflect reality. But then the hard part - since the budget software doesn't also balance our checkbook for us, we have to get the theoretical budget number to guide us regarding what we can do with the funds in the checking account. Even with a list to look at, I have been overwhelmed by how hard it is to keep track of the misc. things we need to reserve money for. When it is all sitting in one pot, it is way too tempting to spend it on something we need right now, and forget about the things (little ones, but which add up) which come due in a few weeks.
We are still using 3 systems - the paper register, which we compare to the bank online, which represents our actual spending, secondly the Quicken budget program, which gives us the tool to "speculate" what we want to spend, and keep tweaking it to reality, and then use it to add the expenses for all the goals we have and get a total, and finally a paper printout of the budget vs. actual, which we generate by inputting the paper checking register into a Quicken account and then running a comparison against the Quicken budget. We can go through and mark up the paper copy and see where we overspent, or where we can cut out something for the month, all in an effort to get the bottom line to zero out. We can modify the budget and then reprint any month's activity including the future month. It helps to have a paper draft.
Now, the worst thing is that despite our goals, we have overspent the budget each month since we started this. We keep dipping into savings while we try to get it to work. And the confounding thing is trying to take the illusive checking balance, and figure out how much has to be left in there after a paycheck is deposited. Since it is not directly linked with the budget program, there is no way to make the two programs give me that number.
And no matter how many times I have tried to ask Bob for help, it hasn't been sinking in for him what it is I want to know. He kept telling me it was impossible to interpret, from the tools we have, what is safe to spend and what has to be held in reserve. WHY THEN DID WE DO ALL THIS WORK? I have the data, I have a budget, and I have notes of our spending events that were outside of the budget.
I refuse to accept that two parallel accounting systems cannot be mated in a way that will tell me how much to spend, or not spend, in order to avoid bouncing a check or consistently exceeding our income. So despite my huge math phobic mental blocks, it finally became clear to me how to figure it out.
Bob's checking account has 5 (savings) sub accounts for separating funds - like a Christmas club. We set values for each of them to reserve money for big revolving expenses like fuel oil, etc. His paycheck will be automatically debited and the funds will be split between the subs before the balance is deposited into his checking act. The actual checking account we use for the things we spend every week like food, gas, and the inevitable medical copays and scripts. The total "goal amount" for those weekly expenses is what I am going to watch for as the target number on the check register immediately after the paycheck gets deposited. (Now that we have a flex spending account we will have to keep the invoices for those, and promptly submit them because otherwise we won't have money for food.)
After all this work, I still had to go back to the savings account and transfer funds electronically to cover the pellets we just put in stock and the overage from our Christmas spending. I'm reserving money for a delivery of fuel oil (though I don't have quite enough for a minimum delivery) and I'm planning a downpayment for our insulation project, which will use up the rest of the savings. At that point we are going to be living out of the freezer if we run out of funds because I'm already paying other expenses on the business side, (like my dental work) so I'm not working enough to generate extra income from my business side.

Maybe after some practice, the other "discretionary" things like clothing and childcare and meals out will find their niche in this system. For now, there isn't anything available for those splurges anyways. But at least I'm finally getting a feel for this and also seeing some of the areas where Bob and I need to grow in order to adopt these kinds of habits in an intrinsic way.