I've been doing a bit more experimenting with iWeb, and so far I'm largely very impressed. It's pleasingly straightforward to use, produces attractive web pages and photo slideshows out of the box, and contains lots of nice polish that I'd not necessarily have expected from a brand new "1.0" release. I expect I may continue to publish my weblog and the rest of this part of the site as I have been, since I like the process I've managed to put together and actually enjoy having the educational/creative opportunity to do a little HTML and CSS tinkering once in a while. (No, really. Apparently I like suffering that much.) But I'm sold on using iWeb to start handling all my photo publishing. Which should help solve the little problem of the pictures page that I haven't gotten around to adding to for, um, nearly three years now...
One minor iWeb annoyance is its habit of generating URLs that contain long GUID strings in place of the site and folder names you specify. By which I mean things like:
http://web.mac.com/troy_stephens/iWeb/814A88D4-4BCF-4433-8387-A03467882948/Welcome.html
It turns out that this is iWeb's way of avoiding non-URL-friendly characters (a legitimate problem that all web publishing software must somehow address). iWeb knows how to escape spaces using %-escapes — e.g. "My%20Other%20Page" — but certain other characters in a site or page's title will cause it to give up and use an auto-generated GUID string in place of an escaped title string. Unfortunately, apostrophe is among the characters that trigger this behavior, making a common title choice like "Bob's Web Site" produce an unpleasantly long and obscure (though otherwise perfectly serviceable) page URL.
Hopefully the substitution logic can be improved in a future iWeb release. In the meantime, sticking with basic characters in your titles will enable you to keep your URLs short and tidy. Unaccented alphanumeric characters, spaces, dashes, underscores, periods, and the '+' charcter are all considered safe by iWeb, as I would have expected since they are intrinsically valid URL characters that don't require escaping. I haven't systematically tested other punctuation characters to see whether they trigger %-escaping or iWeb's GUID replacement (no particular desire to do that at the moment...), but the next time iWeb generates a big string of hex digits where I had hoped to see a recognizable page title, I'll have some idea what to look out for.