Well, as a proportion, I'd say that this has much more to do with compensation than anything else.
Why? Because there are a lot more shoestring/support websites with this problem than there are those which are "well-funded."
The other factor is that branding/redesign work isn't actually web-design,
per se. It's graphic design and marketing work as much as technical web design.
So yes, outdated color/font/layout is a problem in a lot of websites. Most gifted websites fall under that umbrella as well. Then again, most "fringe" support for ANYTHING does.
Unless... it has $$$$ behind it. Then the pros get involved. Otherwise, it's mostly volunteers, and volunteers have limited time and energy to devote to these things. I also strongly suspect that graphic design/arts and marketing are not areas which draw gifted in large numbers, or when they do, those people are often doing several jobs at once, leaving little time to apply those skills on a volunteer basis. As we all know, there isn't much $$ in gifted education.
I've also noticed (and this is just anecdotal) that the overlap between technical skill (even rudimentary) and that marketing/design savvy on the human/soft side is relatively RARE in any population of people, gifted or not.
The other factor at work here is that the entire notion of webdesign has veered toward social media clearinghouses like FB, Twitter, Pinterest, etc.
The result is that even with established "brands" there isn't a lot invested in periodic redesign or updating to message boards, stand-alone informative sites, and the like.
Managing an active message board is actually more work that it looks like, leaving little left over for prettying things up on a regular basis with a small (or all-volunteer) staff.
Of course, momentarily Jon will come and post that it's due to gifted people being Retro (and therefore cool) without even trying.
