ROBERT McCULLOUGH, president of an influential umbrella group representing some 20 neighborhoods in Southeast Portland, figured he might have an in with Mayor Charlie Hales when it came time to lodge a sensitive complaint with city hall.

"The good news is I know the mayor," McCullough joked with the Mercury on Thursday, October 23. "I live four blocks from him. He knows where to find me."

Earlier in October, his group, Southeast Uplift, had sent Hales and the rest of Portland City Council a blunt letter raising pointed concerns about the city's new rules for short-term rentals, including those offered through the controversial listings website Airbnb.

One concern was deemed particularly "worrisome": Despite finding some 488 short-term rental listings within Southeast Uplift's footprint—from Montavilla to Buckman to Sellwood—the group says it received just nine applications for official licenses along the lines of the city's new rules.

And the group joined that finding with a request for something Hales has been decidedly loath to consider: actual and meaningful punishment when hosts or listings sites fall short of the city's new rules. Like, for instance, when they fail to register—a seemingly common violation, according to Southeast Uplift.

"We have adopted this odd set of rules," says McCullough. "But is anyone paying attention to them at all? The answer appears to be 'no.'"

Southeast Uplift's letter arrives at an important time for Portland City Hall, which is mulling over rules for a proposed expansion of short-term rentals to apartment houses and condominiums, first detailed by the Mercury ["Help with Baggage," News, Oct 8].

(Those rules would put a cap on available units and require explicit consent from landlords—and they would join existing rules for single-family homes that call for smoke detectors and permits, and a guarantee that any rooms for rent are part of someone's primary residence.)

Other advocates have voiced similar concerns about enforcement—on top of fears that allowing property owners to offer long-term units for short-term use will deepen Portland's housing woes.

Whether any of that fretting makes a difference remains an open question.

Hales' office, which didn't immediately remember receiving Southeast Uplift's letter, says it won't budge on beefing up enforcement of short-term rental violations absent a groundswell of support from the rest of the city council.

That stance is driven, in part, by financial realities.

"The council may say they want to have dedicated resources" for active enforcement, says Hales policy director Jackie Dingfelder, a former state senator who's been asked to find as much consensus as possible on the proposed new rules. "But it's not in the current proposal."

Right now, the only way the city might know if something's amiss is if someone lodges a complaint. Actively seeking out and policing unlicensed rentals—which may or may not pass safety inspections or have a property owner's permission—would require dedicated staff. And the job would still be a pain.

Workers would have to spend hours combing through listings and digging out addresses, which aren't immediately made public on sites like Airbnb, and then cross-check those addresses against the city's permitting records, says Mike Liefeld, boss of enforcement for the Portland Bureau of Development Services.

Inspectors might even have to call hosts directly to (awkwardly) ask them to volunteer that information.

That would all be a lot simpler if the city, as part of its new rules, insisted on obtaining an up-to-date roster of hosts' addresses from Airbnb and other listings sites. But Airbnb has traditionally challenged attempts to obtain that kind of data. Although Portland's revenue bureau collects hotel taxes from Airbnb, it's allowed to ask only for limited lists of addresses, for audit purposes.

"If we're adding this large new issue, and it's a priority," says Liefeld, "then we have to talk about what we can't do or what new resources are necessary."

But some of Hales' resistance comes down to philosophy. He's also worried about stepping on the neck of a new market he's come to cautiously embrace.

"The mayor," Dingfelder says, "is concerned about over-regulation and putting a chilling effect on this opportunity economy."

Sources say Hales has already raised Airbnb's ire by agreeing to keep a citywide cap on short-term rentals in apartment and condo housing—no more than 10 percent of a building. Bowing to earlier concerns about enforcement, Hales has promised to issue a report in 2016 that looks more deeply at violations and affordability.

But city commissioners may yet force some changes.

On Monday, October 27, the mayor's office met with bureau staffers and representatives from all four commissioners' offices to see what issues had emerged since the proposed rules for apartments and condos were formally released on October 20.

Sources familiar with the discussions tell the Mercury that enforcement—especially how to pay for it—was a big subject. Commissioners could attempt to demand addresses from listings sites, to make things easier. They might also try hiking the cost of a permit for apartment and condo dwellers. Hales has proposed $100 for a two-year permit, short of the $180 charged for would-be hosts in single-family homes.

Tax revenues also came up in those discussions. Bloomberg this month reported that Portland is weighing legal action against listings sites VRBO, HomeAway, and FlipKey amid concerns they're not paying as much as the city believes they owe in hotel taxes. Thomas Lannom, the city's revenue director, declined to tell the Mercury how much the city's taken in from short-term rentals since July 1, citing state law.

McCullough, the president of Southeast Uplift, acknowledged that his neighbors have yet to receive any formal complaints about dangerous or troublesome listings—despite their eagle-eyed report showing hundreds of Airbnb's hosts still seemingly content to be scofflaws.

But if city leaders don't get more serious about enforcement, he argues, it'll be a matter of time.

"It's the law now. We don't oppose it," he says. "But now that we have it, we want to do it right."