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Most investors don’t plunk down hundreds of millions of dollars for a company in an industry that’s awash in troubling trends that are seen by most observers as permanent problems.

But that’s what Aaron Kushner and his Boston-based 2100 Trust did in July, when it struck a deal for the Orange County Register, six other daily newspapers and various other publications owned by Irvine-based Freedom Communications Inc.

Kushner won’t say what he paid for Freedom in the deal, which the Business Journal estimates at $200 million, with the Register accounting for about 75% of the price. He will acknowledge that it’s a contrarian play when it comes to daily newspapers in metro markets, a segment of the industry that has been in a steady decline that began in 2006, well before the recent recession.

“Certainly the margins will not be what they once were, and I don’t think we have a different view from anyone else on that,” Kushner said. “I do not believe that the industry is stable—a stable industry is one where revenue is flat.”

The Register is an exception, according to Kushner, and so is Orange County as a whole. He said the Register was “nicely profitable” and trending upward before its sale.

The industry as a whole continues to see revenue declines.

Estimates from mid-2011—gleaned from information made public when Freedom was in negotiations to sell the entire company—indicate the Register had an operating profit of about $20 million a year at the time.

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Now Kushner is out to grow the Register, adding hires for sales and in the newsroom, where a rugged stretch that included a stint in bankruptcy had cut staff by about half.

Among the changes in the newsroom: more than 20 new hires, a business section that has been restored as a standalone, and various other regular features that have been added. Room for coverage of high school sports has increased dramatically, comics now run in color, and the opinion section has grown to three pages a day. An auto reviewer and restaurant critic have been hired, coverage of pro and college sports have been bolstered, and a movie critic is expected soon. A Sunday magazine for the Register is in the works, according to Kushner, and recent talks around OC points to the acquisition of other local publications.

Where’s the payoff?

Kushner talks in generalities, citing Orange County’s enviable demographics and diverse economy as fertile ground for circulation. That, he says, should lead to more ad sales.

“All we really are at the end of the day is deep believers in the importance and value and power of major newspapers like the Orange County Register,” he said. “I don’t think that’s a particularly magic formula—it’s more a belief system.”

Not everyone sees that as enough. Editorial upgrades hold the potential to build circulation but are unlikely to bring additional ad revenue in the near future, according to Kevin Kamen, a 32-year veteran as a newspaper consultant and owner of Kamen & Co. Group Services in New York.

“I don’t think the financial valuation of the company will grow,” Kamen said.

Orange County’s demographic are desirable, but they’re not unique, according to Kamen.

“Suburban America,” he said, citing Austin, Texas, as a comparable market.

The Austin American-Statesman laid off about 200 employees, more than a quarter of its total staff, about a year ago.

The Register does have demographic strengths— “an educated community, good readership, good base,” Kamen said.

But that’s a moving target, he said, especially when viewed against Kushner’s bid to emphasize the Register’s print product after several years that saw the publication work to push its digital presence. The Register closed its interactive group, which was dedicated to sales and brought in about 10% of advertising revenue, shortly after Kushner took over, according to a source familiar with the situation.

The loss of most of the revenue from the interactive group, along with the additional newsroom costs, have likely meant a significant hit to profits, the source said.

“I respect what he’s trying to do but he just has to juggle a few things at the same time,” industry analyst Kamen said. “He can’t focus on just print and editorial. He needs to be focusing on digital as well. People turn to their smartphones and laptops for news.”

Kushner is typically vague when it comes to the question of print versus online for the Register, although he says little to dissuade the general perception that print is the main driver of his plans.

“Some people ask if we’re a little crazy,” he said. “The short answer is no. Digital is necessary, but it’s not sufficient.”

The Register does plan to put its digital offering behind a paywall, a move that’s expected in coming months.

Kushner offered no specifics on the plan.

He’s mostly mum on his personal life, too. He said he plans to move with his family to Orange County from Boston at some point in the future, and will commute for a Monday-through-Friday workweek until then.

Kushner declines to discuss specifics of his prior business experience, which included a recent stint in the greeting card business.

He’s said to be interested in buying more publications, including the Los Angeles Times.

His politics seem to lean Democratic, according to some in OC electoral circles. He’s given money to several Democratic politicians, including President Barack Obama, Vice President Joe Biden, and onetime presidential contender Howard Dean. A check of records showed he’s also written checks for Republicans, including Senator Susan Collins of Maine and former Minnesota Senator Norm Coleman.

How does Kushner describe his politics? “Private” he said.

He has said he will continue to honor the Register’s Libertarian heritage, providing that perspective a consistent voice on commentary pages. Plans call for more perspectives, too, and Kushner said he sat in on more than 200 editorial board meetings in advance of this week’s elections (see related OC Insider item, in the Nov. 5 print edition of the Orange County Business Journal).