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Helen Ying, a community organizer, educator for 30 years and former Metro Council candidate, has an emotional tie to Old Town Chinatown.

When Ying was 11 years old, her family left Hong Kong for the U.S. She didn’t live in Old Town Chinatown, but it became a lasting connection to her ancestry. So, she was surprised to learn its reputation from a former student.

“He said, ‘Mrs. Ying, what are you doing here? This is a dangerous part of town,’ ” said Ying, who is also an Old Town Chinatown Community Association board member. “It shouldn’t be that way.”

Ying is now involved in a broad-based planning effort by city, community and business stakeholders to address those kinds of sentiments, and create a strategic road map for revitalizing one of Portland’s oldest neighborhoods. The push is part of the West Quadrant Plan – a piece of the Central City 2035 plan that focuses on seven areas: the Pearl District, Goose Hollow, the West End, Downtown, South Downtown, the South Waterfront and Old Town Chinatown.

With regard to redevelopment, Old Town presents significant hurdles. Crumbling and vacant historic buildings need costly upgrades; surface parking lots consume entire blocks; businesses share sidewalks with homeless people waiting for social services; and zoning guidelines are inconsistent and discouraging to new development.

The concept of a New Chinatown/Japantown started with two design charettes at the White Stag Building this month. During the first charette, Wieden + Kennedy Creative Director John Jay and Historic Preservation League of Oregon Executive Director Peggy Moretti gave presentations on the neighborhood’s untapped potential.

“The idea was to get people excited about the neighborhood again,” said Karl Lisle, a senior planner for the Bureau of Planning and Sustainability. “There’s a lot of fatigue there. They’ve been facing a lot of these issues for decades.”

Developer David Gold knows it well. He announced this week that his plans to renovate the Grove Hotel, at Northwest Fourth Avenue and West Burnside Street, as a hostel were kaput after investors withdrew. He said the project depended on securing a restaurant tenant to occupy the ground floor, which was impossible because of the presence of the Right 2 Dream Too homeless camp directly across the street.

“I think it would have been a catalyst; it was a game-changer for the neighborhood,” Gold said. “Who knows? Maybe it will come back at some point, but as of right now there is no project … I would like to see the homeless camp resolved in a humane, equitable manner. I would like to see the city resolve the situation there. That’s the number one priority in the short term. I think most of the property owners and business owners and some of the social service agencies feel the same way.”

The Portland Development Commission spent $3.7 million to purchase the Grove Hotel and make fire-life safety upgrades. Shawn Uhlman, spokesman for the PDC, said the plan was to sell the building to Gold and his partners – including Jay – for $550,000. The PDC also would issue a market-rate loan for $2.65 million.

The disposition and development agreement doesn’t expire until June 30, and Uhlman said the PDC is still negotiating with Gold, despite his claims to the contrary.

“It’s absolutely a challenging project, but it’s not dead,” Uhlman said. “We’re operating against the June 30 expiration of the DDA. But I would say we’re still having discussions. I think David would agree with that … Every side is still interested in seeing this thing move forward, but the challenges are very real.”

Conflicts like that create difficult propositions for investors in Old Town Chinatown. But for all its problems, the neighborhood has even greater potential, said Patrick Gortmaker, project manager of Kalberer Co., which owns key assets like the PDC’s office on Northwest Fifth Avenue, and the annex next door.

“If you look at the infill opportunity left in the city on vacant land, Old Town Chinatown is at the top (of the list),” Gortmaker said. “There’s nowhere else to go than here. How do we do that in a thoughtful process that achieves infill development, contributes to two historic districts, and helps preserve the many historical resources in new Chinatown/Japantown, and Skidmore and Old Town? It’s a difficult question.”

One of the problems is that Old Town Chinatown is actually two overlapping historic districts.

The Skidmore/Old Town Historic District is listed for its architecture; New Chinatown/Japantown is more culturally focused. Gortmaker said a challenge will be identifying which buildings should be listed as contributors to their respective districts.

The Dirty Duck didn’t have that luxury. It was razed to make way for the Blanchet House of Hospitality. The Dirty Duck was listed as a contributing building, though some stakeholders argued otherwise.

“That was a really nasty process,” Gortmaker said. “None of us want to go through that again. So, now is the time to look at all the contributing buildings and really identify the ones that are worth saving.”

Another issue is the neighborhood’s missing teeth – surface parking lots that aid businesses, but discourage pedestrian-friendly redevelopment.

Moretti is working with an ad-hoc group of stakeholders – including John Russell of Russell Development Co., and SERA Architects founder Bing Sheldon – to generate ideas that would incentivize parking lot redevelopment. She said the group would present its work in the next few weeks.

“The surface parking lots are the big elephant in the room,” Moretti said. “They make more money in parking than they do as a developed site … We need to address the economics that are working against redevelopment.”

Catalytic developments in Old Town Chinatown since 2000 include the University of Oregon’s White Stag building, Mercy Corps’ global headquarters and the Oregon College of Oriental Medicine’s building. Peter Englander, PDC’s city manager, thinks the growing presence of educational institutions will help the area gain momentum.

A key development for Ying is the Lan Su Chinese Garden, which she said set the cultural stage for the neighborhood. In the planning effort, she’s representing many of the Chinese restaurateurs who rarely have time to participate in daylong events like design charettes. The planning process is expected to unfold over the next 14 months.

“I think all the challenges that are there can be tackled,” she said. “What we need is leadership, vision, funding, and people behind the work. If we can get all those four (things) we can make it happen … and of course we need the political will from the city.”