Enterprise IA and the convergence of web/hybrid/software

As design for software and design for web continue to merge (AJAX, Flex, etc), I find myself searching for the connections and disparities between the two.

What is navigation in terms of software? What is a task-oriented website design? Is there a need anymore for the click-wait-load-click-wait-load navigation model? Can context for task and space be given through users’ past actions, current needs, and visible future?

Besides the philosophical questions, there are also the practical ones. How much cost difference is there between launching software vs. hybrid vs. website? What is the requirements-design-development-launch cycle like for the three? How do they each fit into an enterprise?

I’m going to continue to poke around at these things and post as I meander my way through.