When San Francisco District Five Supervisor Vallie Brown was appointed in July, she had a lot to figure out, particularly how to balance the demands of city governance while keeping her grassroots ties to her neighborhood.

Now, nine months later, she’s facing a different task: fighting for re-election against a formidable opponent, Dean Preston. He’s a well-known, progressive activist with the campaign experience that Brown lacks — he lost the seat in 2016 to London Breed, Brown’s predecessor, by only 1,800 votes out of 41,000.

And this time, he’s determined to win.

There are still nine months until the November election, but Preston already has a full staff and campaign posters in windows around the district, and he’s raised more than $100,000. His aggressive, early entry into the race has jump-started a district campaign that normally wouldn’t ramp up for another few months.

Preston’s decision to run as a democratic socialist has put Brown in a tricky position: While she calls herself a progressive, she is often tightly associated with moderate Mayor Breed, who appointed her to the seat Breed had occupied. But now, as the campaign ramps up, Brown is scrambling to prove both her aptitude for the job and her independence from the mayor.

“It is what it is,” Brown said, as she shrugged her shoulders and smiled on a recent afternoon. “It’s off to the races.”

District Five is a diverse collection of neighborhoods with myriad problems. Over the years residents have grown increasingly weary of rising home prices, tent camps, discarded needles, street trash and car break-ins. There are copious store vacancies on Haight Street and constant turnover of expensive storefronts on Hayes Street. Meanwhile, the Fillmore and the rest of the Western Addition are struggling to maintain and rebuild their dwindling African American populations.

There was a third candidate, City College trustee Shanell Williams, but she dropped out last week, citing personal reasons. She had raised only about $4,500, according to the latest Ethics Commission filing. Brown has raised about $93,000.

Brown and Preston say they are a good fit for the position because they come from a background of neighborhood activism.

Preston wrote Proposition F, the June ballot measure that gives tenants facing eviction the right to a lawyer, and is the founder of Tenants Together, a statewide renters’ rights group. Brown got her start in the neighborhood by picking up trash from Lower Haight sidewalks on her own accord. She served as a legislative aide for several years, first to former Supervisor Ross Mirkarimi and then to Breed when she was a supervisor.

But which candidacy will thrive in the largely progressive district? A man who brands himself a democratic socialist or a woman who worked in City Hall for years a legislative aide and then as a supervisor?

“The broad ideological issues in this race will be less important than the core neighborhood issues, like vacant storefronts and bike lanes,” said Jim Ross, a longtime political consultant. “How each candidates deals with all those issues and how they present them will have more of an impact.”

Preston, who moved to the district more than 20 years ago, said he has a better shot this time because he’s not running against Breed.

“The times have changed,” Preston said over coffee in a Hayes Valley cafe. “With Breed, we had to make the case of not just why vote for me, but why not vote for the incumbent. And I don’t think that appointed supervisors have earned that level of deference.”

He said his decision to run as a democratic socialist — a buzzy political ideology that supports initiatives such as Medicare for All, tuition-free college and the Green New Deal — is a way to show that he would prioritize the community over corporations.

But that’s also a risky association. While Democratic Socialists of America membership surged around the country after President Trump’s election, the organization is sometimes regarded as polarizing. It’s also not an automatic buy-in for progressive support.

“Being part of the DSA doesn’t earn you an automatic endorsement of working families any more than being part of the Democratic Party does,” said Rudy Gonzalez, executive director of the San Francisco Labor Council, which did not endorse Preston in 2016. “What earns people the endorsement from working families is where they stand on important issues, like access to affordable health care and living wages.”

Still, Preston’s focus on progressive politics will probably make Brown’s association with the mayor a major point of contention during the campaign.

Head start on cash Months before the November election, the District Five supervisor’s campaign is off to a pricey — and early — start. Here are contributions raised from Jan. 1 to Dec. 31, 2018: Dean Preston: $102,732 Vallie Brown: $93,228 Source: San Francisco Ethics Commission

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“Since Vallie was appointed by the mayor, that is something that people who don’t feel as comfortable with London Breed will focus on,” said Tes Welborn, treasurer of the Haight Ashbury Neighborhood Council, who is supporting Preston. “And that will probably shade her one way or the other. People who like London will probably support Vallie. And vice versa.”

Brown said she has an amicable relationship with the mayor and is also independent from her.

“Are we aligned on a lot of social justice issues? Yeah, we are,” Brown said. But Breed “knew we had a lot of differences. She could have appointed someone who could have aligned with her on every step of the way, but she really wanted to make sure that the district had someone who knew it and would take care of it.”

In a statement, Breed said Brown has been “committed to the district for decades.”

“In all her years working in City Hall, she has always put the needs of residents before anything else,” she said. “That is why I thought she was the right person to be appointed to serve.”

While Brown is not considered part of the board’s core progressive faction, she has demonstrated some independence from the mayor. She supported Proposition C, a November ballot measure that Breed opposed, which would raise $300 million in taxes from the city’s largest businesses to fund homeless services. Brown also withheld her support from the mayor’s plan to spend all of the windfall money on homelessness and housing. Instead, she sided with her board colleagues on a proposal that added funds for teacher salaries.

Brown’s colleagues describe her as affable and pragmatic, someone who cares more about the neighborhood than backroom politics. Her few pieces of legislation include increasing the affordability requirements on the Fillmore Street and Divisadero Street neighborhood commercial transit districts.

Another proposal would create a Vehicular Navigation Center pilot program to provide people living in their cars or RVs with a safe place to park overnight. Meanwhile, she said she is working on securing a spot for a Navigation Center on Haight Street.

But Ross, the political consultant, said she has yet to produce any splashy legislative accomplishments that will gain widespread attention from voters. And her time is running out.

“There is a window that kind of closes for her in June or July, where she then won’t be able to do anything without it being seen in a very political way,” Ross said.

Brown’s supporters, however, say she is above fray and focuses on helping the community rather than making big political wins.

“She doesn’t come off as someone who wants to run for the next thing, and the next thing and the next thing,” said Corey Smith, co-founder of Haight Ashbury Neighbors for Density, who supports Brown. “She also has no desire to deal with the political bulls— at the expense of getting things done.”

But even with her accolades as a supervisor and friendly neighbor, Brown’s most enthusiastic supporters are worried about the strength of Preston’s campaign. He already has several endorsements from Brown’s colleagues: Supervisors Aaron Peskin, Matt Haney, Hillary Ronen and Rafael Mandelman.

And in 2016, he really didn’t lose by that much.

“It’s going to be a coin flip,” Smith said.

Trisha Thadani is a San Francisco Chronicle staff writer. Email: tthadani@sfchronicle.com Twitter: @TrishaThadani