As a hiring manager I'm always skeptical when I get a resume filled with "technical" classes from one of the myriad of technical schools around the country. When I've worked with graduates of these programs it seems they have a marginal, but usually satisfactory, understanding of how technology is supposed to work. The problem is I rarely need people who can work with technology that is working. If technology is working and things are simple there is little that end-users need. Even relatively simple tasks like deploying computers depends upon a specific understanding of the complex situation that is most business networks. Few organizations do a "out of the box" installation of a Microsoft Active Directory and run 100% machines that work in that environment. These complexities mean a technical manager is quickly looking for skills that don't come from these technical schools. Ironically because they do tend to come in people who are self-motivated to learn the technology any way they can often the requisite skills are stronger in those who haven't been through this sort of program.
So what does this have to do with Dreamweaver? A friend recently commented that when they look at resumes they similarly discount the web credentials of anyone who lists Dreamweaver, Front Page or other similar programs on their resume for much the same reasons. Usually they've gone to a class or two on web design and don't really understand the web my friend explained. It is far more important that a person who is going to be using the web heavily and designing for the web understand how the web works, what a are key factors in search engine optimization, organic marketing, usability, content management systems and customer service than an understanding of how to use a particular piece of software. In other words the conceptual body of knowledge is far more important than how to push buttons in a software package.
Extrapolating into the mechanical world the Dreamweaver and Front Page slingers of the world are shade tree mechanics. Many of them very good and able to put together quite pretty things and make things look good. Just as many a shade-tree mechanic can do wonders on that '67 Mustang the Front Pager can put the shine on a '97 vintage website. If '97 works then you're done. When it comes to working on the '06 Prius the shade tree mechanic is at a distinct disadvantage. Though at it's heart there is a gas engine, the HTML of the automotive world, there is a much more complex system in play that takes more tools and understanding than the average shade tree mechanic possesses. If you want a '07 website that can keep and build audience and become the business tool you need then you'll do what those in the know do and use a content management system. Best of all when you want an '08 website your job will be much easier.
Of course I am far from the first to raise this point. And it would be wrong to take away the idea that Dreamweaver doesn't have a place. It is a great tool for designing a site even if it is a poor tool for maintaining the content on the site once it is designed.