A handful of people fed up with conditions in downtown Bend took their frustration to City Council recently. The list of speakers included business owners and residents of nearby neighborhoods, and the incidents they recounted would surprise few people who’ve lingered at Riverfront Plaza, hustled through the breezeway connecting it to Wall Street or skirted panhandlers on crowded corners.

One week later, on Wednesday, a city government entourage that included three councilors, City Manager Eric King, Police Chief Jim Porter and a member of the city’s legal staff attended a meeting of the Downtown Bend Business Association. Business representatives asked for clear guidance, including a list of options for dealing with behavior by transients and others that threaten, as one argued, to make Bend’s downtown look like Portland’s. The city officials offered good intentions and uncertainty.

Anyone who thinks cleaning up downtown will be simple or easy should prepare for disappointment.

People who engage in obnoxious behavior may make downtown unpleasant for visitors, not to mention business owners. But they have rights, too, and courts have recognized these rights in weighing efforts taken by cities to keep downtowns civil and orderly. For this reason, a city legal analysis conducted this month concludes, constitutional land mines exist for ordinances aimed at camping, loitering and begging in public places. So, too, with so-called sit/lie ordinances, which prohibit people from sitting or lying on sidewalks.

The city isn’t entirely without recourse. It can help pay for the engagement of private security officers and the installation of cameras that might discourage offensive and illegal behavior. Given time to fill vacancies, the police department can provide a greater presence downtown. The city also can continue to make use of its downtown exclusion zone, an area from which people who’ve committed certain crimes may be banned for up to three months.

Of course, the fact that problems downtown persist despite the exclusion zone’s existence says something about the efficacy of the limited number of management tools that create no constitutional problems. Consider the man who assaulted Bellatazza owner Stewart Fritchman in 2016. Fritchman mentioned the incident and the offender, Netjo Djukanovich, in his written testimony to City Council Aug. 2.

Djukanovich was convicted in Deschutes County Circuit Court of fourth-degree assault in October 2016. He was on probation for that offense in late October when he assaulted Fritchman in downtown Bend. He was convicted of the second assault in December 2016 following a no-contest plea, according to the state’s criminal records database.

Following his assault of ­Fritchman, Djukanovich was released from custody. During that time, he had at least two run-ins with Bend police. On Nov. 11, he was cited for disorderly conduct. On Nov. 17, he was arrested in downtown Bend for kicking and damaging a car door. The arresting officer noted in his report that Djukanovich had been excluded from downtown a couple of weeks earlier for assault and disorderly conduct. Djukanovich said he was aware of the exclusion, according to the police narrative, but “said he just got ‘bored’ so he walked through downtown.”

The lesson? The effectiveness of downtown management policies hinges to a large degree on the willingness of their targets to abide by them. Some may comply, but others may not. And if the combined efforts of cops, courts and local policymakers can’t keep someone like Netjo Djukanovich from spreading misery downtown, it’s naive to think an easy solution to lesser crimes against civility lurks just over the horizon.

That isn’t to say business owners and policymakers should give up. On the contrary, merchants should continue to press the issue, and local leaders should be open to constitutionally defensible proposals to curb the worst behavior. Every little bit helps.

At the same time, business owners should continue to look for creative ways to help themselves. How, without violating the law, can they make downtown a less welcoming environment for people who make it an unwelcoming environment for everyone else? Working to convince visitors not to give money to panhandlers would be a good start. And Fritchman, who attended Wednesday’s business association meeting, described an approach he’s used recently. He rinses the breezeway, which abuts his business, a few times a day. Not only does this clean the ground, but it encourages loiterers to move. People, it turns out, don’t like to sit on wet surfaces.

The city attorney at the meeting called Fritchman’s solution “creative … environmental engineering.” If there’s one good idea out there, surely there are others.

— Erik Lukens is editor of The Bulletin.