I'm extremely excited about a new budget system we're trying out - BucketWise. It was written by Jamis Buck, who actually used to work at BYU on the same team as Ryan, and it's basically everything we've been wanting. When we were first married we used Quicken, but that didn't allow us to create different categories to sort our money into and then draw from. It was a decent way to track overall spending and make sure we were syncing up with our bank account, but it didn't really do what we wanted. And once our version became too old to download online account information we stopped using it.
Next we tried the YNAB approach without buying the YNAB product. Ryan coded up a complete clone of the YNAB spreadsheet where we could enter our purchases into a register, dole money out to specific categories, and it would record how much was spent, budgeted, and remaining in each category. If we went over in a category it would subtract that amount from our available amount to budget in the next month. This worked pretty well except that there was no way to account for different bank accounts. And then Ryan was going to need to roll it over for the new year (I didn't have the time or inclination to learn how to do it myself), but he was too busy with school so it never happened. A scary 5 months of not keeping track of our purchases ensued.
Now we've successfully transitioned over to BucketWise (thanks to Ryan allowing me free reign at the Mac for one weekend so I could enter everything from the past 5 months and figure out how the program works). The program allows you to set up multiple bank or credit card accounts and then you can create "buckets" within each acount. For us, I have all deposits go into a "general" bucket and then I can dole it out from there. With this program I can tell exactly what we can afford to pay for from our main account and what we'll need to pay for from our secondary account (where my paychecks go). I'm hoping this will gradually end the worries about if we've got any money left in our primary account. We're being better about making sure we have the money for a purchase before we make it - even the little ones, which was usually what caught us before. And we're using it to help us save for items we want to get in the future; we already have a "bucket" for Ryan's drumset! We'll see how it works over time, but so far I'm excited.