My first "real"-ish job was at a web design shop in NYC as a web monkey. Back in those days you did all your own code and all the photoshop etc. (and we walked uphill both ways to the office.) None of this 5 man team to make one little website nonsense and no fancy-pants Dreamweaver to write your code for you.
As time passed, more tools and CMS systems have become available which in theory should make web development and maintenance easier. Languages like PHP have made templating much easier, but in the end someone still needs to create the pages in the first place. CSS remains an enormous pain in the neck despite its many benefits.
As we revamped the website over the last few weeks we found that the second you start introducing complexity--even something simple like a protected file that you get to download after registration it all goes out the window.
Of course there is the possibility that we took on too much. A redesign of the corporate site (PHP) along with the installation of Loopfuse; new functions in the Mule developer site (Atlassian Confluence); and a new customer portal (Mule connected to Salesforce.com) seemed like a good idea but in retrospect might have been a little over the top.
Now that the site is up, we are going to take Matt up on his offer of Alfresco's web CMS.