HelloWallet is a relative newcomer to the personal finance management software scene, and as such, it is arguably the slickest and the most modern. It does the best job personalizing its advice of any we’ve tried, and it’s competent in all other areas. Except for one.

It is also the first PFM to attempt to make its users pay money for the service. This is perhaps its only downfall, but it cuts to the core of what it is to be a PFM. If the guiding ethos of PFMs is: you need to watch every penny you spend, and this is how you get a handle on how to save money for your goals -- college, retirement, vacation, whatever -- then how can a PFM justify a $9 monthly fee when there are free alternatives?

If you’re willing to pony up the money, however, HelloWallet is the best -- well, the only -- PFM money can buy.

Accessibility

HelloWallet has one of the slicker Flash-based interfaces out there. Logging in is a breeze, and it even offers a mobile app for both iPhone and Android.

After a 30-day trial, however, HelloWallet costs $8.95 a month to use -- something no other PFM would dare to do. In fact, most would recommend you cut unnecessary costs out of your budget...

Functionality

The site is slick, and even pretty to look at. You might not be able to pay your bills through the app, but you can do a whole lot of cool stuff. You can tell HelloWallet about your household, and it will even remind you to budget in a gift for your wife, girlfriend, son, whomever, a month in advance.

It’s smooth and easy to use, and more than any PFM, seems well-suited to smartphone use. It also encourages you to think about the way you spend your money and puts you in context with your peer group.

In addition to categorizing your spending, HelloWallet also has a set of different colored flags with labels like “Had To,” “Wish I Hadn’t,” and “Glad I Did” that allow you to categorize your spending in a way that’s perhaps more useful to you -- how you feel about money. A cash withdrawal at a bar ATM at 3:30 AM on a Saturday might just categorize as “Cash” elsewhere: on HelloWallet you can flag that “Wish I Hadn’t” -- or “Glad I Did,” whichever is the case.

Breadth

You can add any sort of account to HelloWallet: checking, savings, 401k, loans, etc. The site even allows users to add other assets. We told it we have $100,000 worth of Minerals and a Picasso worth $11 million, but this didn’t seem to affect the site’s opinion of us with regard to our peers. Well, those aren’t liquid assets, so perhaps that makes sense.

Guidance/Categorization

For all its strengths elsewhere, HelloWallet does rather poorly in this category. It seems to cut off the names of merchant accounts short, thereby making them difficult to categorize. The $30 spent at “Dressler Restaura” might have been easier to categorize were it not truncated. Same for “Graham Ave. Me[ats]” and “Graham Ave Li[quors]”.

As stated above, though, the flags allow for another layer of categorization that other PFMs do not: how you feel about your spending.

Education

The site, on its landing page, offers a long list of Daily Guidance, tailored to your spending and net worth. It sees that you don’t own a home -- maybe you need renters insurance? It sees you paid a fee on your BofA account? -- in encourages you to complain to your bank and threaten to leave! It’s a bit edgier and more personalized than Mint’s similar service.

The site doesn’t do much else to educate its users, however.