With so many moving pieces in your finances, I think you guys need to be planning out in advance what your cash will look like every day. If you don't already have something that works for you (like YNAB?), try this.
Linked is a spreadsheet that (I hope) will help you do that. You can download a copy to your computer to edit or save a copy to your Google account. You fill in the current date and your checking balance. You fill in the average amounts of your expenses (gas, groceries, etc.) in the yellow cells in Row 5 and whether you expect to pay them regularly on a day of the week (Monday, Wednesday, etc.) or on a date each month (15, 23, 4) in the yellow cells in Row 6. You will get a drop-down list for your selection because otherwise a typo would cause issues. Spare columns for other regular expenses are off to the far right. This setup should make it pretty quick to change the month days (I just put in random ones to show you how it works) for the monthly expenses and the days of the week for the weekly expenses. Column K "Big Expenses Coming Up!" is for those odd expenses that don't get paid weekly or monthly, such as property taxes. There is also a column for odd cash inflow amounts, such as a bonus or an income tax refund.
I have filled out what we know of your income and expenses from your case study, with a few adjustments (such as assuming that you are cutting grocery spending to $125/month, not eating restaurant food, etc.), but you can change the numbers as necessary. I have assumed that you get paid twice a month. If you have already cut cable, fix the cable number, etc. I have filled in the $4K of upcoming property tax for mid-March, but please correct this to be the right date and amount. I have filled in $5.83 for the bonus coming up on Friday, but please correct this to the actual net check you will receive. Add in any other regular or odd cash amounts, both inflow and outflow, that you and your wife can think of, along with any planned debt payments that won't be on a regular schedule. Again, I just put in numbers and dates/days to test that this spreadsheet was working. Assume that they are all wrong until you have checked them yourself.
My thought was that this would just be for estimating whether you would have an okay checking balance at every date for the next year. (I have set the minimum checking balance as $300, but you can alter that by changing the "300" in the formula of cell D7 to your dollar amount of choice.) I think that every week or so it would make sense to come back to this sheet, go to the balance on the date you look at the sheet, change the cell color to yellow, and type in the actual balance for that date in the "predicted checking" balance column. That way you can keep going forward and you won't need to worry about moving the big expense numbers or changing past expenses to match what was actually spent (for when you spend less than the amount you budgeted on groceries, for example :) ).
To add more rows at the bottom, copy the last row, highlight 365 or so more rows below it, and paste. If you have questions about how the formulae work, just ask.
You won't be able to choose any date later than 28 for regular payments. Why? Because this is a quick-and-dirty spreadsheet, and right now months like February would just end up with no payments for anything given a date like that. So, I have just added a "Later" option. Any payment/income given this option will pop up on the last date of the month.
Disclosure: This is a quick-and-dirty planning tool. The results are only as good as your input. It probably has errors. Please make sure the results make sense. I am not liable for your reliance on this spreadsheet.
