Architecturally speaking, Southeast Division Street between 12th and 20th avenues resembles a rummage sale.

North of Division, charming half-million-dollar bungalows mix with unsightly underdeveloped land to form the gateway to the tony Ladd's Addition neighborhood. Certain stretches of the street's south side feature a hodgepodge of strip-retail and more humble dwellings. But the contrast between the two sides is not that sharp.

Yet, thanks to Ladd's Addition, Division Street's north side qualifies for city historical protections. The south side does not. And because of this, the two sides of the street have two very different sets of rules—and headaches—for developers and architects proposing new buildings along this busy Southeast artery.

And Division's quirky design divide also illustrates a problem that's becoming endemic to the entire city: Portland's crazy quilt of design-review guidelines makes infill development a crapshoot. It's a problem that's sure to grow as the city's population increases and housing becomes so scarce that historical districts get considered for housing.

On a triangle of land on the north-side corner of Southeast 20th Avenue and Division, local housing nonprofit REACH plans to build a four-story, 26-unit mixed-use condominium on a parcel unused since the Reagan years.

REACH plans to sell 18 third- and fourth-floor units at the market rate of roughly $350 per square foot to subsidize eight low-income units on the second floor that will sell for a third of that price. But officials with the nonprofit say one of the city's two design-review boards, the Landmarks Commission, could make that difficult.

Because the city designated Ladd's Addition a historic district in 1998, the $6.4 million project must pass muster with the Landmarks Commission's eight volunteer members—who are mostly of the historic-preservation bent. Ladd's Addition is one among 13 historic districts in Portland, covering an estimated 6.5 percent of the city. (See accompanying box.) The city can declare a district historic, or the neighborhood can petition for historic status.

REACH is seeking approval from the Landmark Commission by August. So far, REACH says it has incurred an extra $15,000 in design fees to incorporate changes in the exterior suggested by the commission, including window placement and the inclusion of stucco or brick. The design review also means that the project will take at least two months longer than projects that don't have to undergo review.

Plus, commission members have indicated in informal feedback that they want the condos reduced to three stories instead of four to protect the scale of Ladd's Addition, where the average home price tops $600,000, according to Realtor Jan Caplener.

Michelle Haynes, REACH's director of housing development, says removing a story would kill the project.

"It would be impossible because we are attempting to offer some units at below cost—we need the fourth story because those are the units that will make the project pencil out," Haynes says. "We care what the community thinks, but we have to produce a project that at least breaks even.

"It's a challenge for affordable-housing developers to produce a product that both meets historic guidelines as interpreted by the Landmarks Commission and still make the city's affordable housing goals," adds Haynes.

Had the building been proposed on the other side of the street, it would have been a different story. There would have been no design review.

For example, the brightly painted green-and-yellow New Seasons Market at 1954 SE Division St., on the south side of the street, didn't require design review when it went up in 2004, according to architects at Richard Brown, the Portland-based firm that's designed seven New Seasons locations. Neither did developer Randy Rapaport's ultramodern four-story condo building that's going up six blocks east on the south side of 26th Avenue and Division. "Had it required review, the project would have never happened," says Rapaport.

Jeff Joslin, land use-manager for Portland's Bureau of Development Services—which oversees the Landmarks Commission—agrees that finding a balance is difficult. But he defends the role of the commission.

"We have a community that cares deeply about how it's developing and where it's coming from," Joslin says. "The purpose is to identify the resources we care most deeply about."

Critics counter that those "identifying the resources" can have too narrow a focus. Where should a local agency that regulates aesthetics draw the line between preserving history and blocking projects from happening at all?

And in areas comprising many architectural styles, such as Division Street and North Mississippi Avenue, it's not clear which architectural era the commission should base its rating of "historical significance" on.

"[It] can be conflicting," Haynes says. "Different members have different suggestions, and it's not always clear to a developer or an architect how to improve or refine a design."

District: Year it gained historic status

Skidmore Fountain/Old Town Historic District: 1975

Yamhill Historic District: 1976

NW Thirteenth Avenue Historic District: 1987

New Chinatown/Japantown Historic District: 1989

East Portland/Grand Avenue Historic District: 1991

King's Hill Historic District: 1991

Rocky Butte Scenic Drive Historic District: 1991

Ladd's Addition Historic District: 1998

South Portland Historic District: 1998

Alphabet Historic District: 2000

Kenton Commercial Historic District: 2001

Mount Tabor Reservoirs Historic District: 2004

Washington Park Reservoirs Historic District: 2004