Untethered
The next point is not a simpler, more intuitive web -- AJAX and such -- but being untethered from the desktop and laptop. This is where the iPod is pointing to and the challenge ahead. It is the ability to work anywhere without having to give full attention to the computer. A device that works naturaly with human beings like the iPod starts to do and has all the capabilities of a desktop system.
Practically this means mobile devices that you can talk and talk back to and have natural input touch devices. A prototype early example of this is TechCrunch's review of Ajay Juneja voice controlled car.
The significance to being untethered is an exponential capability in daily activity. Being able to look up information at the spot where one is when about to give a lecture, contacting someone associated on your network that can deliver a service needed now ("Are you at Fry's computer store?" "Can you pickup a USB cable and we can meet along the way?" "I've authorized you $40 on paypal.") Then people will be able to deliver services to each other as either barter or payment, rather than advertising being the main web model.
This may seem mundane but how much time and effort is used up doing things on ones own waiting to get to the right place and time? The result is an exponential ability to focus and achieve ones goals.