After putting this question out on Twitter today and receiving a bunch of answers, I decided to take it out of the 140 character limit and provide a comment form. Here are the rules. First, you’re only allowed one answer. If you have multiple answers, figure out which one you think needs the most work or attention. I know some of the developer types have an endless list of weaknesses for WordPress but I only want the one that you feel is the most important. Second, explain what you have done to try and fix the weakest link or suggest what you plan on doing.
The more I engage with the WordPress community and consistently browse WordPress.org, the more I feel that WordPress.org itself is the projects weakest link. I’ve harped on this before and I’ll continue to do so until the situation changes. The site is the bread and butter of WordPress. It’s where all of the information is housed, links to resources are presented, clear and concise directions are given, etc. If it were 2005 all over again, perhaps the information presented on WordPress.org would be relevant but in 2009, it’s frustrating to realize how much information is missing from the site. I realize that the site will eventually get an overhaul to turn more into a community hub which I can’t wait for, but as it stands, I think the entire site needs to be reformatted with fresh, relevant content related to the project instead of static HTML pages from yesteryear. With a dynamic project such as WordPress, I don’t understand the notion of set and forget with regards to the website for the project. I expect things to readily change along with WordPress to give a sense of progress. Instead, the site makes me think I’m stuck in history.
Since I consider this to be the weakest point, I’m considering rewriting the pages myself using the Codex to create a rough draft first, as Demetris has done with the WordPress Features page.