If you asked my dad he would never remodel his house. He likes it as it is and doesn't find it necessary. His house hasn't been remodeled since the late 50s.
I agree that some functions of the site definitely work well. I love the way the forums are organized, but the user interface needs a major facelift. There are many that will not welcome a new layout. However, there are a few obvious things that don't follow what we would all consider standard.
- Login/Register link not located top/right is one glaring one.
- Tables (really? It's 2010.)
- Location of the edit link! (below the message or above it, and to the right!)
I don't know if this is fortunate or unfortunate, but the site's brand dates it so much that you do not have to make a change and everyone would be OK with it. I still think of a giant spider wearing bifocals and sitting behind a big pile of computers whenever I see that.
Anyway, I saw a comment in another thread that said "If people want it to look like Facebook, they won't come here." Reminds me of the old "you young kids get off my lawn!" line. I don't think anybody would expect WW to turn into a Facebook clone or be redesigned with grunge elements and reflected logos. All of that stuff dates it just as much as calling yourself a "Webmaster".
But the site doesn't look like a designer ever took some time to consider color, unity, form, space, etc. All of the elements that create a good design are lacking or missing from this site.
To be honest, when I was first learning CSS this site was my biggest help. I can't tell you how grateful I am for it. It really helped shape my future. However, I stopped coming back because I always felt the site was a dinosaur and wouldn't keep up. To see an email from Brett saying they were considering an upgrade, I got excited again.
If there is a major overhaul (backend and frontend) then I am excited for it. If the old farts get their way and nothing changes except maybe for the logo I will definitely be disappointed.