I have been hosting markwatson.com for almost 10 years on the same server using just plain old HTML and a little PHP. It will take a while (I am super busy working on a Ruby book, and some consulting projects) but I am switching the site over to Apache 2.0x + FastCGI + Rails. I will eventually also be using some Java web services on another server for some live demos.
I have kept the structure of my site the same for years to avoid broken links, etc. I have decided to restructure my site, and to heck with broken links, etc. This is an easier decision to make now that many people navigate the web using search instead of bookmarks. I hate to break old links, and I will be a little careful, but change is good.
I really enjoy writing, and I have been thinking of doing more web content writing instead of distributing my free web books as PDF files. About 8 years ago, I experimented with an online Java/AI tutorial using a few Java applets for live examples. I don't use applets anymore, but with AJAX, etc., I can have some dynamic content as appropriate. Another advantage of having all of my web books live on my site instead of releasing PDF files is being able to sprinkle a few advertisements in them for some extra revenue. Ruby has a few good templating systems and I want to experiment with them to get a good fit for supporting separating content of web books from presentation and occasional random advertisement placements. In any case, I am in no hurry, so I can tinker with getting a flexible authoring and presentation setup.