In the two weeks leading up to Bernie Sanders' first major address since July's Democratic National Convention, a flurry of revelations have come to light that put into question the democratic socialist's quest to spark a "political revolution" to combat special interests and the "1 percent" and promote financial transparency.

On Wednesday, Sanders will speak to his supporters to rally support for his new organization, "Our Revolution," which aims to boost progressive candidates seeking office, after the senator set records at the grassroots level fundraising while a candidate for president.

"Thanks to all of your hard work in our campaign this past year we have transformed American politics. On issue after issue — making college affordable, progressive taxation, climate change, trade and many others — more and more Americans are agreeing with us," Sanders said in a press release Thursday promoting his Wednesday address from the Ripley Manor in Washington, D.C., which will also be broadcast live to volunteers at more than 2,000 organizing meetings across the country.

"People are ready to take on the 1 percent," Sanders added. "During our campaign we assembled a movement of millions of people ready to fight for the country we know we can become. Election days come and go, but the struggle for economic, social, racial and environmental justice must continue. We have the guts and the energy to take on the special interests, win critical battles on the most important issues of our time, and redefine what's possible in this country."

Sanders began fundraising for "Our Revolution" earlier in the month, getting behind candidates like Tim Canova, who is running against former Democratic National Committee Chairwoman Debbie Wasserman Schultz, a congresswoman from Florida. But while campaign finance reform might have been a big part of his "revolution," Sanders may be treading into troubled waters with his latest endeavor.

His group functions as a 501(c)(4) organization, which can receive unlimited contributions, according to the Internal Revenue Service, but is supposed to be focused on social welfare. While some involvement in political activities is allowed, it is not supposed to be the main focus of this type of group. Such an organization also does not have to disclose the sources of its funding, which according to OpenSecrets.org could earn it a dreaded "dark money" label, unless the group opts to reveal its donors.

Because Sanders is an elected official and a former candidate for president, at least one expert suggested that the 501(c)(4) group with which he is connected may be constrained by campaign finance laws that limit how much donors are allowed to give and may require disclosure of donors.

"This definitely raises, in my experience, novel campaign finance issues," said Paul Ryan, the deputy executive director of the nonprofit Campaign Legal Center, in an interview with ABC News published Friday.

The senator from Vermont also found himself under the microscope this week when he declined to release his personal financial records, after asking for two extensions during his campaign for the Democratic nomination.

During that campaign, he often called for transparency for money in politics. Yet he was simultaneously citing the rigors of campaigning to avoid disclosure. His rival, Clinton, released her records on time.

The Sanders campaign maintains it did nothing wrong.

"We were told that since the senator no longer is a candidate there was no requirement to file," Michael Briggs, a spokesman for Sanders, told the Center for Public Integrity.

A financial disclosure form would have shown the senator's finances through mid-May of 2016.

In its report Thursday, CPI, which is a nonpartisan, nonprofit investigative journalism organisation, said Sanders "exploited" the system.

"Sanders expertly exploited a system that effectively allowed him to delay, delay, delay — all while he chided Clinton receipt of six-figure paydays for delivering closed-door speeches to officials at investment bank Goldman Sachs and other powerful special interests," CPI wrote.

Sanders did submit a Senate disclosure form in June which details his Senate salary, a "small" pension from the government of Burlington, Vt., where he served before coming to Congress, and a "handful of modest honoraria for speeches and television show appearances, although he reported donating them to charity," according to CPI. The form also showed between $15,000 and $50,000 in credit card debt and $500,000 to $1 million in mortgage debt. However, the disclosure only shows his finances through 2015.

CPI's report followed news that Sanders and his wife Jane bought a third home, a summer house on the lakefront near Burlington for $575,000. Sanders and his wife already have homes in Burlington and Washington.

Jane Sanders told Seven Days that it was the sale of a home in Maine passed down by her family that gave her and her husband the means to purchase the new property.

Still, the news of the Sanders' new home sparked a slew of taunts poking fun at the democratic socialist on social media and in the the wider media, including the Daily Caller suggesting that "capitalism is alive and well."

The New York Post mocked Sanders for putting a "new spin" on "'socialism' in America."

"Bernie Sanders now has one thing in common with the millionaires and billionaires and other 1 percenters he so frequently attacked on the campaign trail: he now owns his very own summer home," read a story from Vanity Fair.