I have a personal Rails site that does something like this. There&#x27;s an Expense model and a Expenditure model. Also a PayEvent model that&#x27;s kinda the opposite of Expense, could probably roll them into one model. The Expenses are averaged out by month. An expense can be &#x27;tracked&#x27;, that means when I&#x27;m adding an individual expenditure, I can list it as that expense. My dashboard tells me at a glance how much I&#x27;ve spent on those expenses. If it&#x27;s not tracked, it is factored in automatically.<p>It is multi-user, though I&#x27;m the only user at the moment. If anyone wants to give it a whirl, shoot me an email which you can find in my profile.<p>My philosophy is to avoid the banking APIs by putting in expenditures manually. I would love to integrate with OFX, but I don&#x27;t have the time to maintain it.