While Democrats and the Obama campaign hound Republican presidential candidate Mitt Romney over a lack of transparency regarding his personal finances, Gawker has ostensibly pulled off a journalistic coup. The oft-mocked stepchild of serious journalism outlets released a 950-page document dump that it claims reveals the uglier crevices of the former Massachusetts governor's investments. (The full trove of documents can be found here).

An early analysis of the files confirms long-held criticisms of Romney's acquisition -- and retention -- of fabulous wealth, despite his not having worked in the private sector since 1999. Some of Romney's millions were birthed by exploiting several weaknesses in tax laws on overseas investments, as well as back-door methods of swapping assets behind the government's back.

Both methods are legal. How politically damning any of this may be remains to be seen. But in the case of the Bain files, we know being Romney Rich isn't simple. But it's a lot more profitable than working a 9-to-5 with a 401k.

A spokeswoman for Romney responded to the document dump, telling Politico, As we have already disclosed, his retirement agreement included entering into passive investments in Bain entities for 10 years, through 2009. In 2002 he created a blind trust in accordance with Massachusetts ethics rules after he was elected governor. Gov. and Mrs. Romney do not control the investment of these assets, the investment decisions are made by a trustee.

Gawker's files release consists of internal audits, financial statements, and private investor letters for 21 entities that Romney pumped $10 million or more into as of 2011. It also brings with it the heavy burden of deciphering and interpreting the contents, a process journalistic organizations and financial gurus are likely undertaking at this moment. Together, the papers paint a somewhat clearer picture of the GOP nominee's estimated $250 million: where it is stored, how it is managed and how it has grown or shrunk over the last few years.

Romney's personal finances have received an excruciating level of attention, after the nominee released his last two tax returns to the public. While Romney argues he has met the legal obligations of any candidate, his adamant refusal to open his books further only helps the Obama campaign paint the picture of an entitled private equity tycoon, which could damage his standing with an electorate still shaken by a Great Recession. That Romney, and his wife Anne, have steadfastly maintained he will not release beyond the required amount has only added to the mystery.

In the absence of concrete documentation provided by Romney, speculation has filled the void. Romney's storage of some funds overseas is known, though the extent is uncertain. It's also known that Bain, the private equity firm he started in 1984, continues to be his main source of investment income long after he left the company in 1999.

To understand the value of the documents and Romney's investment, one must first get a clear sense of what exactly Bain Capital is and how it functions. Contrary to popular belief, a private equity firm does not resemble a marauding beast made of money that gobbles up an existing business, heartlessly spits out a sizable chunk of its workforce, and regurgitates a better-run, possibly profitable company -- though the Obama camp won't dispute the description.

Instead, Bain and entities like it manage a slew of similar enterprises under the auspices of specially created partnerships and holding companies which funnel money back to the private equity firm like any classic investment vehicle. Many of those funds inevitably meet an imposed terminus, typically after the businesses reach a value that will reward the private equity firm with a sizable profit through, for example, a sale or stock offering.

To Romney, Bain then becomes more akin to an investment bank, except it uses businesses instead of stocks to generate returns. So when talking about Romney's holdings, the real question is which Bain funds -- and the once-independent enterprises they entail -- does the GOP nominee keep.

While some of Romney's personal financial figures are revealed, the real crux lies in the 21 Bain funds he invests in, which are mapped out in the documents. In some cases, convoluted machinations through offshore entities and the exploitation of the low, 15-percent capital gains tax rate emerge. Combined, they allow a man to effectively pay Uncle Sam 13 percent, and not a penny less, on millions gained from investments.

President Barack Obama has offered proposals attacking overseas tax havens like the Cayman Islands. After the Bain Files, the legislation appears specifically designed with Romney in mind.

Because the loophole shielding overseas transactions remains, a hullabaloo has arisen over the extent of Romney's overseas holdings, as Gawker points out. The practice is common, and a somewhat efficient way of side-stepping obligations to the IRS.

The financial statement for the $3.7 billion Bain Capital Fund VIII LP, in which Romney has invested, reads like an anti-tax manifesto. The partnership is a qualified intermediary and intends to conduct it operations so that it will not be engaged in a United States trade or business and, therefore, will not be subject to United States federal income or withholding tax on its income from United States sources. ... Under the current laws of the Cayman Islands, there are no income, estate, transfer, sales, or other Cayman Islands taxes payable by the partnership.

More importantly, several funds Romney has invested in engage in what are known as equity swaps. In layman's terms, the value gained or lost by any investment is kept hidden from the IRS because no actual purchase or sale occurs -- just the swapping of metaphorical baseball cards with the promise to toss in money at a later date.

For example, Romney's stake in the $929 million Absolute Capital Return Partners LP increased $13 million in value when the fund entered into a $288 million equity swap, with minimal tax obligations. The value of Romney's stake in the fund increased with the deal. And while it was technically a transaction, no money changed hands. Tax obligations as a result of the deal were below minimal.

But what immediately becomes clear, according to several published reports, is this: Mitt Romney's money-shuffling is too complicated for most journalists to decipher. That did not stop a few superhuman reporters at Gawker's competitors from immediately dismissing the find. Apparently some can consume 950 pages of dense financial filings within hours.

The punditocracy is right in some cases. Some of Gawker's early interpretations of the documents draw a tenuous connection to Romney, are contrarian for the sake of it, silly, or old news. It's no wonder the site put out an open call for experts to comb through the documents.

CNN Money's Dan Primack argues the document dump reveals little of value. Within financial circles, this may be true. But if the documents allow the Obama camp to map the road Romney's money took around the IRS to the Caymans, the potential for alienating the middle class electorate remains substantial.

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