His cynicism always seemed tinged with a utopian optimism
I agree completely. In light of recent developments like https://news.ycombinator.com/item?id=5285627 you might say that his views are becoming better more widely accepted, even if their history is not acknowledged. In Computer Lib Nelson advocated what we today might call a "Wikipedia" or "Khan Academy" model of education. I'll allow myself to post an extended quotation from his reaction to dialogue-based learning systems because I find the entire thing fascinating and terribly prescient (keep in mind that this was published in 1974):

"The alternative is straightforward. Instead of devising
elaborate systems permitting the computer or its
instructional contents to control the situation, why not
permit the student to control the system, show him how to
do so intelligently, and make it easy for him to find his own
way? Discard the sequences, items and conversation, and
allow the student to move freely through materials which he
may control. Never mind optimizing reinforcement or
validating teaching sequences. Motivate the user and let him
loose in a wonderful place.

Let the student control the sequence, put him in control of
interesting and clear material, and make him feel good—
comfortable, interested, and autonomous. Teach him to
orient himself: not having the system answer questions, all
typed in, but allowing the student to get answers by looking
in a fairly obvious place. (Dialogue is unnecessary even when
it does not intrude.) Such ultra-rich environments allow the
student to choose what he will study, when he will study it
and how he will study it, and to what criteria of
accomplishment he will aim. Let the student pick what he
wishes to study next, decide when he wishes to be tested,
and give him a variety of interesting materials, events and
opportunities. Let the student ask to be tested on what he
thinks he knows, when he is ready, selecting the most
appropriate form of testing available.

This approach has several advantages. First, it
circumvents the incredible obstacles created by the
dialogue-item-sequence philosophy. It ends the danger to
students of bugs in the material. And last, it does what
education is supposed to do—foster student enthusiasm,
involvement, and self-reliance.

Under such circumstances students will actually be
interested, motivated to achieve far more than they have
ever achieved within the normal instructional framework;
and any lopsidedness which may result will be far offset by
the degree of accomplishment which will occur—it being
much better to create lopsided but enthusiastic genius
specialists than listless, apathetic, or cruelly rebellious
mediocrities. If they start soon enough they may even reach
adulthood with natural minds: driven by enthusiasm and
interest, crippled in no areas, eager to learn more, and far
smarter than people ordinarily end up being.

Enthusiasm and involvement are what really count. This is
why the right to explore far outweighs any administrative
advantages of creating and enforcing “subjects” and
curriculum sequences. The enhancement of motivation that
will follow from letting kids learn anything they want to
learn will far outweigh any specialization that may result. By
the elimination or benign replacement of both curriculum
and tests in an ultra-rich environment, we will prevent the
attrition of the natural motivation of children from its
initially enormous levels, and mental development will be
the natural straight diagonal rather than the customary
parabola."