Microsoft Money Plus Deluxe, $39.99 Money is classic Microsoft: Everything is fine, if a bit clunky; nothing is particularly great. I definitely found it to be more user-friendly than Quicken. When you log in, it immediately displays a summary of all your accounts with a chart of spending categories and some personalized reminders. The Windows XP-style interface isn't very attractive, but it's familiar and relatively easy to navigate. In terms of features, Money's a draw with Quicken: There are tools for budgeting, bill payments, and even lifetime fiscal planning.
My biggest complaint is cost: The initial download is priced the same as Quicken, but my bank charged me an additional $10 a month to let Money automatically download data. (I could grab data manually for free, but then what's the point of the software?) Money's security practices may also give some people pause: It stores your bank passwords in a Microsoft data center, and, as CNET has pointed out, it requires a Windows Live ID, which is used for a variety of Microsoft-run services and hence may be more vulnerable.
Ease of Use: 7
Total: 23 (out of 40)
Wesabe, Free Founded in 2005, Wesabe attempts to apply the community spirit of social-media applications like MySpace and Digg to your personal finances. Of course, it does not actually share your financial data; instead, it provides personalized tips based on your spending habits, plus access to a bunch of message board-style groups. I like the concept, but I found the execution spotty at best. The tips in particular were a bust: I'm not jazzed, for example, by the fact that 948 Wesabe users recommend Arby's, where they saved an average of $1.41 per visit over McDonald's. And while I can see the appeal of joining a group devoted to, say, paying down debt, this seems incidental to the site's money-management tools—which, in general, weren't as nicely presented as some of the other Web sites.
Ease of Use: 5
Total: 28 (out of 40)
Mint, Free Mint was the first site I tried, and it remained a favorite throughout these tests. Of all the software, Mint was the easiest to set up, and it has the most cleanly designed and intuitive interface. Its e-mail and text-message alerts work great, and unlike some of its competitors, Mint will e-mail you a weekly financial summary that I found useful—I like being able to look back to see that, despite the global financial meltdown, my net worth actually increased in recent months. (Granted, it's still in negative digits.) Plus, Mint was the only software to support all seven of my financial accounts—none of the others recognized my current 401(k) provider.
But Mint is not without its flaws. Its "Ways To Save" section—which is supposed to provide personalized tips based on your transactions—is more like thinly disguised advertising, repeatedly exhorting you to switch to a lower-interest-rate credit card or sign up for a different checking account. Mint stores users' data on a third-party server, albeit a trustworthy one. And while you can easily assign categories to transactions, Mint doesn't let you create your own—forcing me to classify subway expenditures under "Auto" and visits to the corner deli under "Groceries" instead of something clever like "late-night beer runs."
Ease of Use: 10
Total: 34 (out of 40)
Quicken Online, $2.99/month I disliked Quicken, but I loved its stand-alone Internet platform, which Intuit launched at the beginning of the year. The only thing Quicken Online does wrong, really, is charge $3 a month for its service. In every other respect, this was my favorite by a significant margin. It's the only software that managed to consistently display the most recent balance on my checking account, which was key. It also lets you enter expenses that haven't cleared yet and thus avoid those classic "Oops, forgot all about that check!" moments. Setup and navigation are a breeze. The main page is good-looking, and it has a handy "Am I living within my means?" calculator. (Answer: not really!) The security measures seem reliable. Help is easy to find—and actually helpful. And I love being able to create custom categories for my spending, which allows me to tease out some interesting trends—and occasionally casts harsh light on some bad habits. For instance: Did I really spend more money on wine and liquor in September than I did on groceries? Well, you know what they say: The first step toward change is admitting you have a problem. Thanks, Quicken Online!
Ease of Use: 10
Total: 35 (out of 40)
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