This is Max from Scenic America. This thread came up in my Google Alerts so I thought I'd chime in.
We really enjoyed our time in Pittsburgh last weekend. The William Penn was one most spectacular hotels I've ever stayed in. The lobby is jaw-dropping and there is an astounding mural inside the Terrace Room restaurant depicting the battle of Fort Pitt.
We met at the Allegheny Harvard-Yale-Princeton Club down the block, which itself is a remarkable example of preserved tenement housing sandwiched in between a couple skyscrapers.
In regards to the comment from the article about the newspaper boxes: the reporter was pressing for "something we didn't like," and the boxes were an off-handed comment from one of the board members.
The proposal to digitize the Bayer sign atop Mt Washington is a real cause for concern. To look up at Mt Washington and see a glowing advertisement would be a real shame and would quite literally ruin the view.
For those interested in the billboard issue in Pittsburgh I urge you to join Scenic Pittsburgh. There is a proposal to ban digital billboards and reduce other billboard blight in the city that will be heard on Monday, Nov. 21: Scenic Pittsburgh - Community - Pittsburgh, PA | Facebook
Sorry I don't have more specifics on the legislation or hearing, but I'm sure if you contact Scenic Pittsburgh they can fill you in.