Watch clip #10. I think that Sir Tim had the openness right, but Douglas had the (intermittent) funding and patience of an entity that would not give up on incremental progress. If only it, (linked computers and sharing), could have happened sooner.
Looks like the ability to change the display view is what HTML/CSS is missing right now, but we had in 1969.
Bootstrapping is a good idea as well, but might make the convicts fight the jailers in some situations.
You would probably be well served to allow the mindset of Mr. Engelbart influence your plan. (hint: Watch the whole presentation).