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1. They got flooded with Occupeep entries, and WaPo said an Occupy winner took on an air of inevitability.
2. The winning submission was by someone who "doesn't necessarily agree with Occupy, but supports their right to protest." The Post editors said that her inclusion of accurate signage -- she "wanted to fairly represent Occupy and not make light of their complaints" coupled with a touch that especially appealed to the Post editors according to their winning entry description -- the rats. "I had heard about the rats, and the V for Vendetta mask, so I had to include those," the artist said. Apparently the Post thought the rats showed a willingness to be relentlessly fair and unbiased that distinguished it from the other entries. You know, like the Post itself. 
She must have really done some research if she was unfamiliar with Occupy and included those.
Heck I didn't know until recently what the cat stood for.
It symbolizes Wildcat Strikes and by extension, the 1940's era IWW (Wobblies), the anti-authoritarian leftist union (the main leftist group in the US that was not centralized state socialist, although I suspect that some of the remaining trotskies have drifted over to the IWW position). The cat represents the freedom of workers to strike; the right to strike was made illegal when the Taft-Hartley Act (I think) banned wildcat (i.e. not sanctioned by the bosses) strikes in the 1940s or thereabouts.
[font face="Times"]Apparently, Wobbly Cat's name is Sabo.[/font]
The squatters' rights symbol is a lightning-bolt arrow in a circle and represents Exactly What It Says On The Tin, and is commonly used by political activist punks, since they are the main squatters groups in the US since the days of the 1980s-era Lower East Side, I'm sure you know about that but perhaps others don't. They're basically the successors to the 1960s hippie communes.
I did the IWW poster for instance, but it's just a collage. The rainbow pony is from the cult animation series
Friendship Is Magic and is commonly seen saluting things, engaging in aerobatics, and other manly activities.
She is therefore an icon for the military wing of the fanbase, hackers, and Rachel Maddow fans.
The derpy pony is a creation of Anonymous, based on an animation error in the pilot. She is a
clumsy pony who is functionally disabled, a single mother, and a Postal Service worker. She was
later officially incorporated into the show, which caused iTunes to censor the resulting episode.
[font face="Impact" size="3"]DERPY WAS HERE[/font]
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Lot of barns and chicken coops in backyards there. Good views of the mountains too.
Bend, hmm... I was surprised and disappointed to find out how dry and bare Eastern Oregon was. Coming from the East Coast, it amazed me to find out that folks out on the West Coast are used to the grass and flowers dying in the summertime even in the valley (they have two seasons, the rainy season and the dry season).
I lived at the Kellogg Lake Apartments back when. East Coast for me now but I loved having a lake beneath my balcony at the time.
To Mount Hood. 
I only got as far as Powell Butte.
But I did read they were going to extend the light rail to Milwaukie. Now that I wished for when I lived there. It would have been great to step on a train and head to downtown Portland without worrying about driving back. The light rail runs near where I live now and I couldn't be more pleased. 
Which are turning, by the way. 
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