Yeah, I totally mean that last part. That is the kicking-myself part. I am a passably decent writer, but in this particular instance I actually have more experience and knowledge about the subject than the person who actually wrote about it. My main weakness as a freelancer is not being able to look at a site that I really want to write for and say, "Oh, I bet if I wrote about (x) they would totally publish that."
I write best under assignment. I need to improve my ability to come up with ideas for articles that I can pitch, because once the idea is there I have a fairly good success rate. In fact, I have only written three full-length pieces on spec, and two of them were (eventually) published. Everything else I've written for pay has been assigned, and I once lost a good paying gig because they moved from an assignment-based model to a pitch-based model and I couldn't come up with any good ideas.
This is a flaw of mine, and seeing it play out like the Cracked article about board games today makes me...well, to put a positive spin on it, it makes me feel extremely motivated to work on this area of weakness.