I appreciate the thoughtfulness you've put into this, but I have to disagree a little bit.

First, I am perpetually shocked to find peers in tech who still use BASIC or other tools that others see as outdated. The last one I found was a food product company; their lead tech guy, a member of the family, had given new meaning to NIH with the system he showed me. His website spec document literally started and ended with DO NOT WANT WORDPRESS, in large part, he explained, because he wanted someone who brought the same mindset to technology that he did: Invent something that fits the problem like a glove. And--that probably will not even closely resemble WordPress.

I've since learned that what really happens to influence a technology decision is not trend or "technological progress" alone. At the root of this stuff is human psychology. And not even individual human psychology, but human _relational_ psychology. In some human relational systems you get things like this: A family that is technologically backwards _by psychology_ sells a high-demand food product. They displace all of their technology thinking onto their son, or whoever is even remotely interested. And _that_ person does whatever they're comfortable with and good at. Voila: The rich and hidden empire of yesterday's tech!

And...you want to work with that person, you want that company to give you access to their funding--you have to kind of protect their on-ramp and you even quickly realize: Gosh, it still works and even surprisingly well! Otherwise they will tell mom and dad: "Sorry, we still have to use yesterday's tech." Well: Mom and dad actually love hearing that.

We will always need students who are ready to work with people and companies like this.

So I disagree that raw HTML and CSS are a dying path in a way that rules them out except for that set of new learners for whom it's less "specific problem solving" and more "build a website as you see them on the web". Clients who ask for WordPress these days are sometimes simply asking for what friends told them to ask for. For those building the websites, it can be a golden opportunity to step in and really bring problem-solving skills to bear, where the client can't be bothered to do so. Otherwise you paint a big target on your back for competition with other "WordPress companies" and the like. $300 gets you a new website, that kind of thing.

I absolutely agree about the overall risk of starting students out with an empty Notepad document too. I got into WordPress and Mambo/Joomla back in 2006 and had a blast right up until I was using gobs of plugins for everything and then they started to die, or get bought out by e.g. a company that tried to spam my clients with telecommunications equipment advertisements. What is there to do but start really figuring out how to solve problems without the plugins, in a situation like this? Then I found Textpattern, which was an amazingly great way to start dipping toes into template design and eventually PHP and SQL. When I taught people web design at our local college, I made sure they knew the advantages and disadvantages of Photoshop HTML Export, and then taught them how to do it in the best way possible. I gave extra credit points to those who would dive into the code a little bit.