One thing I can suggest is since you're not actually beholden to following any sort of GAAP for your personal book keeping... is it's fine to do whatever works

One thing I can suggest is since you're not actually beholden to following any sort of GAAP for your personal book keeping... is it's fine to do whatever works for you. Use your best judgement. Unless you're doing this accounting for the joy of the task in and of itself, then you've got a set of problems you're trying to solve or questions you're trying to answer and following GAAP doesn't necessarily get you any closer to those solutions in any meaningful way. I'd echo someone else's recommendation to have one place in your hierarchy that has a balance that matches up with each physical account so you can check your work when you've entered all your transactions. Beyond that, you're basically programming a system for processing the math related to your money. You can figure it out. I'd been muddling my way through for years due to the same inability to find any good "accounting for regular people" before I met my SO who is a CPA. Her response to my accounting methods were basically "It's wrong, but it will work just fine." Want to allocate the money in an account to some things? Create some subaccounts, move money into them. What kind of account? Asset! Asset all the things! People sending money that's going into your chequeing account to pay future bills? Create a subaccount (you guessed it - asset) and put the money into that. Your chequeing account's balance matches up, that money is separated. Perfect is the enemy of good.