Sometime last year, podcaster Anneke Rudegeair bought three different brands of condoms. This month, she sat down with TurboTax and listed the cost of rubbers as a deduction. It was, she believes, a business expense.

Rudegair, 28, is better known to legions of fans as Soccergirl Incorporated, the self-described "podcasting librarian with big tits." Her job, for which she grossed $22,000 in 2007, is to show off her charms on her site and purr about all things sexual in her podcasts.

So there's an argument to be made that the Future-Condom Challenge she and her boyfriend undertook was part of the gig.

"What otherwise would be your regular life becomes your business life; that's been true for podcasting since the beginning," said Rudegair, of Germantown, N.Y. "It's all legitimate."

Nice work if you can get it. Which, technically, is the central conundrum of new media pioneers and their accountants at tax time: In an age when bloggers and podcasters are making a living – or trying to – by blogging and podcasting about their personal lives, what exactly is legitimate? And if writing off your personal life is as easy as writing about it online and getting some Google ads, why doesn't everybody do it?

The Internal Revenue Service certainly doesn't make it clear. A request for information was met with directions to a page at IRS.gov entitled Business or Hobby? Answer Has Implications for Deductions. There, the public is informed that "an activity is carried on for profit if it makes a profit during at least three of the last five tax years, including the current year."

Broadly, the notion is you have to make some money. But there's no further details concerning the IRS' views on how living one's life in public apply to expenses that are "common and accepted in the taxpayer's trade or business."

It's a topic so new, it confounded a number of legal and tax experts contacted for this story. A spokeswoman for the Office of Tax Policy Research at the University of Michigan's Ross School of Business said her experts couldn't comment because, "As we move into new technology, it's really hard to know about some of this stuff."

"I hadn't really thought about bloggers, but they're basically making their personal lives their businesses," said John Robinson, an accounting professor at the University of Texas' McCombs School of Business. "When you make expenditures that are primarily for business purposes, then it's deductible. If it's primarily personal, then it's not. As for the experimental use of a condom, you have to ask, would she have engaged in these extra expenditures were it not for her work? I honestly don't know how I'd apply that rule. This is plowing new ground."

Indeed, those in the field are feeling their way as the mediums mature. Rudegair said she was nervous the first time she put "podcaster" on the form as her occupation, worried that "they'll think it's a made-up thing." And Mike Yusi, who produces the twice-weekly music show UCRadio out of his Los Angeles home, illustrated the difficulty defining whether his show is a hobby or a job by indicating that he "would do it whether I could write it off or not, but once the possibility to offset the costs came up, I jumped at it."

Rob Walch, coauthor of Tricks of the Podcasting Masters and host of Podcast411, agreed there's some gray area.

"If you were to go to get a manicure or massage and you blog podcast about it and you are making money on the blog or podcast, you could write it off," Walch said. "But that does not mean you will not get audited."

That's the rub, said New York blogger Julia Allison, who writes extensively about her personal life at her And Another Thing… blog and in her work for TimeOut New York. The IRS, she quipped, will audit a podcaster who expenses condoms "just for fun."

"The IRS doesn't understand, isn't interested in understanding that your personal life can sometimes merge with your professional life," she said. "It has to be 100 percent business. If there's even a small percentage that is for your personal life, you can't expense it."

Many play it safe. Dennis Gray of San Luis Opisbo, California, host of the parenting podcast 101 Uses For Baby Wipes, often receives free products for review. To avoid the tax consequences of receiving those items, he gives them away on the show when he's done.

"That makes it a wash, an income and expense at the same time," he said. "I don't want to have to declare all that nonsense, book it as income, use it as income, calculate appreciation and turn around and sell it. So I get rid of it to avoid the tax man."

For Rudegair's part, she said she hesitated to deduct much early on but now she puts down such items as those condoms and outfits she buys for her web videos as well as such traditional business expenses as computer equipment, home-office space and travel related to promoting her show.

"I don't know if I'm going to get in trouble for this, but it's defendable," she said. "I mean, I'd love to show the IRS which episode I did what I did in."