Years ago, my wife and I used to religiously enter everything from our checkbook into Quicken. Unfortunately, we did very little analysis of how we were spending beyond "too much" or "just right." We knew exactly how much we were spending, but not why or where.
Years have passed, and we have become even worse about managing our money. When big or out-of-the-ordinary chunks of cash (bonus, consulting, whatever) come in, we're good at applying that to car loans/etc. such that we have no debt beyond our mortgage. But we still stink at managing our money, in part because we don't have anyone advising us on how smart people manage their money.
So, today, I gave Wesabe a spin. I've known about Wesabe well before it became a company, having discussed it with Marc Hedlund while he was still an EIR with O'Reilly Media. The basic idea: harness the power of a community to analyze one's spending and to get collective help (tips, etc.).