Before I get to the post-encampment stage as such, a bit about homelessness and how it affected Occupy.
The first thing that happens when you put up free housing in a city center and provide free food is that homeless people settle there. The homeless people that I saw in Occupy were generally not disruptive, but with rare exceptions they were functionally apolitical. People who become homeless in the U.S. primarily because of poverty are engaged in a desperate scramble to negotiate what supportive resources for them exist and to find work. If there is temporary housing or shelter space available, they are in it, not out on the streets. The long-term homeless who sleep on the streets and for whom an Occupy camp is a step up are primarily homeless because they have serious mental health or substance abuse problems. They can barely get through society as it is, much less mobilize their energies effectively to make changes in it.
And Occupy, being a middle-class movement, dealt with homelessness pretty badly. Occupiers everywhere were proud that they didn't kick homeless people out. They could hardly do so in any case, given that all-inclusiveness was a major ideological component of Occupy. But the homeless weren't in general really full participants and everyone knew it, although there was something of a taboo against admitting it. I talked to a number of people who came back to the town that I lived in after Zuccotti Park was cleared, and a lot of them were more or less openly relieved that it was gone, because they were tired of keeping the camp going for people who had no real interest in Occupy's ideas. The right-wing media were always on the lookout for anything resembling an atrocity story coming out of an Occupy camp, so the non-homeless people there had to be unpaid security and social workers and shelter maintenance with no training or interest in doing what was essentially charitable rather than political work. One of the best weapons that the top 1% had was in making us take responsibility for the bottom 1% that they had abandoned.
The Occupation that I was involved in had a whole second attempt at an encampment. The liberal college town we were in, after saying we couldn't have tents at the public park, helped to broker an encampment on the grounds of a downtown church. Unlike what happened in New York, a local church let us set up on their grounds. But they had conditions, like "no active protesting or literature distribution" and "quiet at night" that made it a depository for tents, not really an active encampment as such. We were supposed to go back to the public park in the day for any political activities. The group agonized over whether to accept this through weeks of General Assemblies and finally did. But by then the group had grayed significantly, as the young people who'd been looking for jobs had found them and dropped out. Only a few people were left who actually could take sleeping in the tents in the winter, and after a couple of weeks the tents were only occupied by the homeless. And then there was a full outbreak of middle-class anxiety. Someone found needles in one of the tents, and there were rumors of people getting drunk and someone coming close to an overdose, and people suddenly had to confront the unremarkable fact that homeless people who have been kicked out of shelters are generally substance abusers. Rather than trying to get them treatment, people insisted that we were being irresponsible for setting up a place where they could do this unmonitored, so we closed the encampment and the homeless people presumably went back to the woods.
I don't think that dealing with homelessness was the critical problem for Occupy. The short-term problem was the police. But it certainly didn't help that a major component of people in Occupy thought that we should get rid of the encampments anyways, even before the police drove us out. The attitude after the evictions wasn't one of completely unrelieved outrage, for a lot of people it was "All right, it was time to do something else anyways. Let's go on to the next thing." People didn't have magical foresight, of course, and didn't know that there really was going to be no next thing. But it was certainly was a factor weakening the movement at a critical juncture.