Verizon, facing saturation in its wireless services business, wants to diversify its revenue mix and become a major player in mobile media and advertising. But it faces numerous obstacles on the path to realizing the vision of becoming a prime mover in the sector.

To get there, the telco is looking to cobble together the 1 billion-plus monthly users of Yahoo, which Verizon is acquiring for $4.8 billion, with of AOL, which it purchased last year for $4.4 billion. Verizon sees a rich opportunity in funneling content and advertising from those and other properties to its 100 million wireless subscribers, and crack into the mobile-ad market dominated by Google and Facebook.

“We have a pretty clear set of goals for 2020, and the main one is to get to 2 billion users,” AOL CEO Tim Armstrong said in an interview. “Facebook and Google are looking like real juggernauts, but that doesn’t mean we can’t be a strong third competitor.”

On paper, the strategy makes sense, according analysts — even though Yahoo’s net revenue is on track to decline 14% in 2016. Verizon’s acquisition of the Yahoo Internet businesses is targeted to close in the first quarter of 2017.

“Yahoo will provide an immediate boost to the nascent Verizon mobile platform with additional content and increased advertising scale,” Cowen & Co. analyst Colby Synesael wrote in a research note Monday. “All in, the combined AOL/Yahoo platform should provide a level of scale that makes it a more meaningful player than either company was alone.”

Verizon is banking on boosting mobile-advertising views with Yahoo’s core focus on sports, news, and finance info, as well as its email service. Yahoo also brings additional ad-tech tools to what’s already in the AOL arsenal, including the BrightRoll ad-serving platform, Flurry mobile apps and analytics, and Gemini native and search advertising platforms.

But while Verizon is placing its bet on becoming a media behemoth, the challenge will be in the execution, said Peter Csathy, founder and chairman of Creatv Media, a media investment and advisory firm. “If Verizon can tie in AOL and Yahoo together, and empower AOL and Yahoo to be really drive the media strategy, then it has the opportunity to succeed,” he said. “But that’s the big trick.”

So far, consumer interest in Verizon’s mobile-centric video service, Go90, which launched last fall, “has been tepid,” according to a note from UBS analysts led by John Hodulik.

Together, AOL and Go90 make up less than 3% of Verizon’s revenue; adding in Yahoo, that will still be less than 6%, according to the firm’s estimates. “While this deal will barely move the growth or margin profile of Verizon, synergies over time could provide upside to earnings,” the UBS analysts said.

And the telco faces a potentially big and thorny problem: Consumers have a more negative perception of how Verizon treats their privacy and data, compared with Internet companies like Google and Netflix, according to Steve Beck, founder and managing partner of New York-based management consultancy cg42. The firm’s recent surveys of a panel of 18,000 U.S. consumers found that 35% of respondents said they trust Verizon with their personal info, compared with 42% for Google and 43% for Netflix. (Facebook was not covered in the firm’s latest wave of surveys.)

“Verizon is acquiring eyeballs relatively inexpensively… by rounding up the greatest hits from the ’90s and early 2000s,” he said, “this isn’t a slam dunk.”

The survey results “paint the challenge that Verizon has as it really goes deep in the ad-supported space with a free business model. The perception is that they don’t have the same trust in privacy that companies like Google have,” said Beck.

Meanwhile, another major job for Verizon – and for CEO Marissa Mayer, for the time being, as she continues in her role through the close of the deal – will be to restore employee morale, Csathy said.

“The first trick will be to improve employee morale in the face of inevitable job cuts” from the combination of AOL and Yahoo, he said. Verizon “has the potential to change morale – Yahoo has been an unhappy place for quite a while. It’s critical for them to retain the best people, and bring in the right talent to stitch all these pieces together.”

Yahoo’s merger into the Verizon fold will be overseen by Marni Walden, the telco’s exec VP and president of product innovation and new businesses, with Armstrong taking the lead on integration. Armstrong said he and Walden will be meeting with Mayer and other Yahoo execs this week to begin determining strategic priorities and management roles going forward, a process he said would take anywhere from 3-6 months.

What’s also important to recognize is that Yahoo has actually been losing share of mobile advertising spending to Google and Facebook. In 2016, Google will snare 31.7% of the U.S. mobile advertising market, followed by Facebook at 19.2%, according to estimates from eMarketer. Yahoo’s mobile-ad share is expected to decline to 2.5% (versus 2.9% in 2015), while AOL’s Millennial Media barely registers at 0.3%, per eMarketer.

On the business-to-business front, Verizon has an opportunity to pitch advertisers as an alternative to Google and Facebook, said cg42’s Beck. But “they would need to go really deep on what the niches, business practices and policies are where Google and Facebook are vulnerable to attack… and how can they create a viable alternative,” he said.

One of Verizon’s key differences is that it’s leading with producing and acquiring content, such as its MLB free game-of-the-week and a separate deal with the NHL. By contrast, Google and Facebook’s businesses are based on monetizing content created by others. The issue there is that creating or licensing content is a lower-margin and more capital-intensive game.

In addition to its acquisition of AOL, Verizon earlier this year formed a 50-50 digital-video joint venture with Hearst, and the JV subsequently bought Complex Media. Verizon also took a 24.5% stake in AwesomenessTV, majority owned by DreamWorks Animation and Hearst holding the remaining equity, and the telco’s execs plan to roll out a premium subscription offering for Go90 with original series from AwesomenessTV.

How all these pieces come together to catalyze Verizon’s overall mobile-media play — or not — remains to be seen. As for how Yahoo’s traffic will feed into the equation, Armstrong noted that Yahoo Sports is second only to ESPN in digital audience, with 7 million daily users, while 43 million visit the Yahoo homepage daily. All told, Yahoo will bring 165 billion “daily data events” across devices to the AOL-Verizon data set, according to Armstrong.

In any case, RBC Capital Markets analyst Mark Mahaney sees the Verizon deal for Yahoo “as signifying something of an ignominious end for Yahoo, which used to be ‘he Facebook’ or ‘the Google’ of the Internet circa 1999,” he wrote in a note. The exit for the web’s erstwhile powerhouse “says something about the key importance of robust and long-term investment ramps — a la Amazon and Google and Facebook, and arguably unlike Yahoo and eBay.”