I'd really like to see some screenshots when you have something to show for your efforts! It sounds like you have a good approach. We can generalize the principle of focusing on the minimum complexity required to move to the next milestones: "If you don't have to think about multiple things together, then don't!"

Also, I can sympathize with your web development struggles. My web development skills are still stuck back in the 90s. I've had refreshing them with all this AJAX goodness on my todo list for a while but I've managed to distract myself with work on the back-end/systems side so far.

Truth be told, I was hoping secretly hoping that by the time I got back to web development the tools would have improved sufficiently so I didn't have to concern myself with more arcane, low-level black magic. That has happened to a degree. Browsers are much more compliant these days. It used to be that you had to spend most of your time tracking down bugs specific to one browser or another.

When I get back to this, my plan is to start by researching in depth the low-level fundamentals, so I can go down that rabbit hole if I need to, but mostly I'd like to spend most of my time leveraging high-level Javascript compilers such as GWT and Pyjamas.

Thanks for the link to unobtrusive Javascript. Looks like a pretty sweet approach!