Part of my interest in creating Maple Leaf 2.0 was learning to use Wordpress and see if I could quasi-teach myself how to customize a blog. So far, I've been impressed with the community and the resources available, although there are so many sources for plug-ins, themes, etc., it can be a time-consuming, embarassement of riches (perhaps there's an opportunity for someone to create a well-designed, user-friendly WP portal if it doesn't already exist). Clearly, WP is a powerful platform with lots of flexibility if you have some programming knowledge and/or you're willing to invest some time to learn the basics. As a long-time Blogware user, I now have new appreciation for Blogware's feature-rich platform - although I'd like to see it become a little more flexible in terms of customization and its ability to work with other services such as Measure Map and Feedburner (note: anyone know how to configure FeedFlare or Measure Map within Blogware?).
   Another thing that struck me about Wordpress is Matt Mullenweg's strategic vision and how it plans to turn Wordpress.com into a business. To date, Wordpress.com and an increasing number of plug-ins are free. From what I understand, Matt plans to introduce fee-based services but I have yet to see any sign of this plan materializing. You have to wonder if Wordpress's angel investors will put pressure on Matt to accelerate his fee-based strategy?
  While Wordpress.com is a clean, user-friendly service, I'm not convinced it can make the leap from free to fee. I'm puzzled why, for example, Wordpress.com keeps introducing new widgets/features that make the free service more useful because it only creates more reasons for people not to pay for anything. Perhaps some of these new features will convert to fee over time, or perhaps there are some sexy, new features (standalone or packages) on the way that will come with a monthly subscription fee. In an ideal world, Matt could become the Craig Newmark of the blogging world if he can develop a few services that attract a critical mass of paying customers. At the same, however, I fear Wordpress could easily fail to become much of a revenue-generating business. This will mean Automattic (Matt's holding company) will have to look at other ways to make money.