If someone uninvolved with Wikipedia was following the news on Wikipedia, what kind of headlines on the news articles about Wikipedia would he see? More or less, he would see: "Jimbo Wales Financial Troubles/Philandering" (and...sexual exploits, and some troubling issues with his ex's article), "Village in Englad falls to Vandalism (about vandalism, which was immediately reverted after the story came out, to a page, which is now significantly improved, about an English village) "Parents of High Schoolers Criticize Wikipedia" (relative to the threats posted to the HS in California's page), "How Wikipedia Can Rip You Off" (based on a completely uninformed blog post, but it was on the front page of Yahoo), "Pro-Israel group slanting Wikipedia"...on and on the list goes. It's amazing how much bad news get around about Wikipedia.
(A footnote: It doesn't help that the reporters can't even get their facts right. The LA Times article about the threats on the HS page got fact wrong. The article quoting J.B Murray about WP:MMM was egregiously inaccurate. It is extremely ironic that Wikipedia is viewed in the public eye and lambasted in academic circles as inaccurate, yet the very article about it (from websites that are supposed to be accurate) sometimes contain numerous errors.)
I really think that the PR problems have to do with the public's fundamental misconceptions about Wikipedia. If you can stretch your memory to remember yourself as a newbie, then you will remember the confusion you faced. There were all sorts acronyms being used (AGF, COI, ANI, etc.), names of prominent Wikipedians being tossed around, and you were confused. Wikipedia definitely has a very steep learning curve.
Most new users attempt to write something they know about, and they don't know the first thing about formatting, referencing (don't even talk about the MOS), and usually their articles or contributions get speedy deleted or flagged, and they get warned. The official policy is WP:BITE (another abbreviation), but in practice, we "Dracula" the newbies all the time, even if we are patient and polite (and a lot of veterans aren't).
Many of this comes because people don't understand the really, really complex rules of Wikipedia. To illustrate, take a look at the (very few) web pages that are more visited than Wikipedia. You've got search engines, with extra features (Google, Yahoo, MSN), an auction site (Ebay), and other site. Basically, they are websites that are quite simple to use. Meanwhile Wikipedia just blows new users away, almost literally. It is definitely not what you would call "user-friendly".
However, beyond the complex rules (which, by the way, I'm not complaining about; they are usually great, and necessary; however, they are undeniably hard to learn quickly for new users), there are the news stories, as I said above. It really amazes me that Wikipedia can have so much bad press, yet everything goes on as usual.
(Another footnote: One of the latest of bad reports is that Wikipedia is a "porn-peddler". One of the main images they mentioned was the "Virgin Killer". The image was nominated for deletion, and it the result was an overwhelming keep, per policy. I'm not going to argue with the policies, but I think that if it is true that the FBI is investigating if Wikipedia is violating child-porn law, then the image should be taken down. It really doesn't matter what the policy is, keeping it gives the impression that Wikipedia consists of a bunch of pedophilists and stubborn law-breakers who won't listen to common sense. After all, Wikipedia is supposed to be an EDUCATIONAL tool (and the Wikimedia spokesman said that they were Wikipedia "target group"), and Virgin Killer.jpg cannot even be defined as being educational.)
So, what am I saying? I don't know; perhaps this means that all the bad news is an indicator that Wikipedia is now too big for any one event or person (even the omnipotent Jimbo Wales) to affect. However, I think it may prove the opposite: I really don't think that Wikipedia can get so much bad press and continue as usual.