Once again I have attempted to be a customer of a news organization’s online advertising system, and once again I am left wondering if such systems were designed by incompetents or sadistic, anti-journalism geniuses bent on our industry’s destruction. Part of my local paper’s attempt to combat craigslist is to offer free ads to anyone seeking to unload things for $300 or less. I have a couple of pieces of furniture, they have gotten no response on craigslist, and I’m not yet ready to just donate them to the thrift store, so I thought I’d place one of these “Cool Cheap Stuff!” ads (yes, there’s no comma between cool and cheap, so immediately you know no one ran the page’s name past anyone who got good grades for grammar and punctuation). The page in the paper says the online system for placing an ad is “easy-to-use” (again, yes, it is hyphenated even though it is not modifying anything) and available 24 hours a day. Turns out, it is neither.
As a potential customer, the whole experience left me exasperated.
As a news person, it absolutely enraged me. If I did my job as badly as the person who designed that ad system did his, everything that passed in front of me would be rearranged and rendered into dingbat symbols. On the news side, we have to give everything at least a second look, usually more. The equivalent online I would think would be answering the question, “Does this thing work?” Because no, this thing did not work. If getting revenue from online operations is the future of the news business, this kind of thing fills me with despair for the future.
Newsroom With A View 
I also am very frustrated with “Cool Cheap Stuff”, as I cannot post. I know many buy the paper for that section. I continue to get an “item too big” error. There is no site administrator to find out what the error means. Richmond Times Dispatch wants payment to help. It is supposed to be free. As I cannot post ads I don’t want them to store my information, but cannot find a way to delete my account. If it is a site issue it could be fixed, but it is easier to have us call in and charge us for the ad.
I no longer work for any company related to the Richmond Times-Dispatch, but I had a similar experience to yours when I lived in Richmond. Try emailing tsilvestri@timesdispatch.com
Follow-up. After much fooling around on the site I found that “item sold too big” means this: There is a second page to posting an ad. This is for website listing. At the bottom you are asked to list the item, but if you put too many words in that section, you will not be allowed to place the ad at all.
Oh I get that now from the error message. Hope this saves someone else some frustration.