I think it happened quite a bit earlier (perhaps 2005 -> 2010), at least when you look at some of the "prime" web properties. Gmail or Google Docs in 2010 were already pretty close to what we have today. Hard to believe, but XMLHttpRequest actually dates back to 1999! JSON isn't much younger.
I don't think the models of web development have changed dramatically since the publication of TTW. There are some other, more incremental changes that aren't reflected in the current edition - there are two examples in my other comment here (Service Workers, parser harmonization, etc) - but by and large, the content should be still largely relevant.
I've wrote my Engineering Thesis when I was studying on PJWSTK (around 2006) about passive fingerprinting based on your tool (p0f), we've created our custom fingerprints for p0f also. Thanks for sharing p0f and afl with the world, great tools!
I'm not working on one right now and have not talked to the publisher about it. So not in the next couple of months. In the longer haul - maybe probably?
Having just recently worked with a flash app again (third party integration..) - I'm not sure if the bogus and dangerous idea of "trusting the client, because it runs" your" code" is new, exactly...
Then again, I keep pointing out that in addition to rest, there's a architecture for "movable code" in Fielding's paper as well (and rpc, as distinct from rest).
