I can definitely understand Obama's hesitation to embrace OWS. It wasn't entirely clear if they'd appreciate it. However, what he could have done, was to speak out about the OWS protesters freedom of assembly. He has the highest executive office in the land. He was silent as local ordinances swept aside 1st Amendment rights. He says a lot of good things. IMO he believes these things. But, personally, I'm not inspired by his action.
It's an interesting list to look at: http://en.rsf.org/press-freedom-index-2011-2012,1043.html