Searching for the best online tax-prep service on the market.

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March 16 2010 7:12 AM

The Taxman Cometh

My search for the best online tax-prep service on the market.

Illustration by Mark Alan Stamaty. Click image to expand.

Taxes, as we all know, were invented by Barack Obama to ruin America. But until the tricorn-hatted hordes rise up and unite from sea to shining sea, we must fork over to the feds, thereby supporting a host of socialist boondoggles such as schools and roads.

At least online tax preparation services make this outrage less painful. And there are a bunch of them, too, all promising "easy filing," "expert advice," and "maximum refunds." How does one determine which of these services live up to their adjective-laden hype? You could complete your taxes using each of them, take notes, and compare the results—but what sort of nerdy masochist does that?

This sort right here. Admittedly, I took a few liberties along the way. For the record, my legal name is not Edward Awesome. Nor, technically, is my occupation "malingerer." Other than those minor embellishments, however, I stuck strictly to the financial facts—which are exceedingly average. I am neither a farmer nor a fisherman. I do not have a foreign bank account. I did not spend any portion of 2009 in a combat zone. I have no gambling winnings or royalty income. Instead, I have a wife, a kid, a job, a house and some very modest, not to say laughably tiny, investments. My taxes aren't as super simple as they were in my freewheeling youth, nor are they as complicated as they'll be once I make it big in malingering.

Methodology
I did my taxes using each program, entering the same earnings, deductions, etc. I used the "help" features often and went back to make changes in order to see how the programs would deal with a curveball or two. I kept rough track of how long each took and noted the number of times I felt confused or had to read something more than once to understand it.

Ease of use (10 points): I want my hand held. If I felt confident about doing my taxes I wouldn't be using an online service. I would fill them out on paper, place the forms in an envelope, and strap that envelope to a D.C.-bound carrier pigeon just as my grandparents did.

Helpfulness (10 points): Although the IRS famously makes the taxation process crystal-clear, each prep system offers online support to help you if you're bewildered by, for example, the difference between a 1099 INT and a 1099 DIV.

Value (10 points): Cheaper is better, sure. But if shelling out 20 bucks means that I get a bigger refund, or don't get audited, then that's an Andrew Jackson I'm willing to spare.

The results, from taxing to terrific:

H&R Block at Home: $14.95 (Basic)

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I half-wonder whether H&R Block at Home is a ploy to convince you that doing your taxes at home is impossible. Because they make it feel that way. The bulleted list of documents it says you'll need is long and includes stuff most of us simply won't, like alimony and unreimbursed job-expense records. It's intimidating from the get-go.

When I signed up, the program encouraged me to download the latest version of Firefox, which I did. But even after that, the column names didn't always align over the columns themselves and, in general, the layout and navigation was a mess. I tried Safari, too, with similarly dismal results.

The program asks questions like "Did you pay interest on a student loan in 2009?" But there's no place to answer yes or no. Instead, there's a link that says "Add Interest," which takes you to another screen, which then asks whether you have a 1098 form, without offering any description of that form. The help menu bar asks whether you have a substitute statement, but is that the same as a 1098? Where am I?

Throughout the unpleasant process, I had the discomfiting sense that I was leaving out an important figure or failing to check a crucial box. My paranoia deepened when At Home suggested that I upgrade from basic to deluxe multiple times even though, from the description, the basic plan should have sufficed.

Ease of use: 5
Helpfulness of advice: 4
Value: 5
Total: 14

Tax Slayer: $9.95

I'm assuming from the name, and from the fact that the company sponsors a NASCAR driver, that Tax Slayer has a certain demographic in mind. I'm also assuming that it thinks this demographic will be impressed with its "Extreme Refund Generator"—which, unlike other refund tallies, includes the word "extreme."

So I was surprised to find that the Tax Slayer video guide is a middle-aged man in a red tie who calls himself Bobby. Not a knight who can slay my taxes in an extreme fashion but, rather, bland-old Bobby, who assures me that he'll be right there throughout the process in case I have any questions.

Setting aside my qualms with Tax Slayer's marketing consistency, I still found Bobby rather disappointing, because he was not "right there" when I needed him. After he introduced himself, I just couldn't figure out how to bring him back. And I could have used some guidance. When you complete a section, the program returns you to a main menu, but I wasn't sure where to go next. Each section has a little icon indicating whether you've entered information, but it doesn't say whether that section is now complete. Do I need to do more? Help me, Bobby!

Speaking of help, the text is weirdly punctuated and often vague. One explanation begins: "There are many important changes that happen during the year that can affect many areas of your life." This, coincidentally, is how I opened every essay in high school.

Ease of use: 6
Helpfulness of advice: 5
Value: 6
Total: 17

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