DAN SALTZMAN was charitable, at first, after listening to his colleagues put the finishing touches on a controversial ordinance meant to legalize (and legitimize) certain types of short-term vacation rentals—something no other US city has dared to try.

Speaking at a Portland City Council hearing July 23, the city's housing commissioner made sure to mention his embrace of the new law—which applies only to single-family homes and backyard granny units. He also took care to say how much he welcomed Airbnb—the nationally infamous rental listings hub (and new Old Town tenant) that stands to benefit most from Portland's legalization push.

Eventually, Saltzman got to his real point.

"We also know it's going to ultimately diminish the number of rooms for rent" in Portland, he said.

And with that flourish, Saltzman announced he'd be resurrecting—and beefing up—an interesting idea his colleagues rejected just six weeks before ["A Good Idea Gone Wrong," News, June 11]: a plan to siphon every cent of tax money raised through short-term rentals and spit them all, instead, into a city construction fund for affordable housing. The overall amount would be close to $500,000 a year.

"There's a clear nexus here," he declared. "The impact may not be large to start with, but it's going to grow."

It remains a bold call. And this time it was publicly welcomed by more than a dozen housing advocates, all of whom backed Saltzman in a press release.

But even with all that, it's still not clear Saltzman will get his way.

On the eve of the council's final vote on short-term rentals this Wednesday, July 30—and a little more than a week before Saltzman's own self-declared August 6 deadline for a decision on his funding plan—his office has yet to line up the votes needed to push it through.

Saltzman already annoyed his colleagues the first time he pitched the plan, sources say, failing to do the kind of personal salesmanship that might have smoothed over any skepticism.

And now, in a time of council grudges over contentious issues like cost waivers for Old Town/Chinatown redevelopment and a bedeviled plan for a new street fee, that quest isn't getting any easier. The only other commissioner to join up so far is Nick Fish, Saltzman's co-sponsor the last time he pitched his funding plan.

Saltzman and Fish have likely written off Commissioners Amanda Fritz and Steve Novick, sources say—and apparently for good reason.

Fritz tells the Mercury she remains steadfastly opposed—arguing that the money Saltzman wants to grab has already been built into the city's budget and spent on other priorities, like the parks bureau she controls. Beyond that, she says, the city already increased the housing bureau's budget this fiscal year.

"Why is he owed another $500,000?" she says.

Novick—who pointedly sparred with both Saltzman and Fish over the street fee plan he's pushing alongside Mayor Charlie Hales—says he's only slightly less resolute in his opposition.

"I'm sympathetic," he says. But his reticence, he explains, has many wellsprings: He's "not totally sold this Airbnb thing will be a great idea," and he's hesitant to see housing money become an excuse to keep the rentals around if they turn out to have too much of a dark side.

"My inclination would be to re-outlaw it and crack down," he says. "It would be harder to do that if was seen as a source of revenue for a noble cause. Just like it's hard to back out of urban renewal now."

He's also worried the sum—$500,000 or so—is too small to justify creating a separate pot of money. He's been privately examining the notion of tapping into a much larger pot: the $21 million he says was funneled into the city's general fund from hotel taxes last year. Half of that money, Novick suggests, could go to housing.

But that might be an even bigger nonstarter, sources say. Because those millions are already built into the city's budget, commissioners would have to make substantial cuts in other bureaus to accommodate that change.

"I tend to think the police bureau is overfunded," Novick says. "I don't want to disappoint advocates.... I'm trying to think if there's a different way to address their concerns."

That leaves Hales, who was reportedly peeved by Saltzman's timing the last time he unveiled his push for housing money. Saltzman and his chief of staff, Brendan Finn, sat down to sell the mayor almost immediately after the July 23 council meeting adjourned.

Hales' spokesman, Dana Haynes, says the mayor is always, generally, "persuadable." However, Haynes says, there's "no indication yet" of Hales "making a move on this issue."

Finn, Saltzman's chief of staff, says his boss won't stop pushing, despite the long odds.

"There's a pathway there," Finn insists.

Outside city hall, some advocates who'd been expecting victory are trying to keep some semblance of optimism. Others are just fuming.

Rich Rodgers, a longtime staffer for former Commissioner Erik Sten, cites city hall's longtime struggle to find a substantial and permanent funding source for affordable housing. He calls it one more example of the city's underfunded infrastructure.

"The pressure's not abating. Rents are way up," he says. "This is a scrap to acknowledge we have failed for 20 years to find even a modest answer to one of our most significant problems. And to balk at this is incomprehensible to me.... It's not leadership."