The scenario you're describing is exactly what we focus on. Ultimately, there are three different ways we "spend" money. There's how we
want to spend money, there's how we
think we spend money, and there's how we
actually spend money. A good expense tracking / budgeting tool is going to bring all three of those circles into alignment. Also, our opinion is that the tool shouldn't be too complicated. Most people only need 1% of the options Quicken gives you. I have more opinions on it, but I won't flood HN with them right now.
I probably won't be checking this thread super-often, so if you (or anyone) have any questions, or if there's a specific feature that you need to have available in a budgeting app, ping me on Twitter.