Regarding the jargon, I agree with wedrifid that LW-specific jargon is actually being defined as the sequences, and from what I've heard and experienced this is extremely helpful in setting down a common language for us to discuss these matters.
However, there is some jargon that could and probably should be done away with: the computer science stuff. Not all sequences/articles have it, but when it's there it's usually several levels of inference away from laypeople. The CS/programming examples, comparisons and metaphors are fun for someone like me, but it's an accepted matter among IT people that things like the XKCD comic on a random function that always returns 4 will not help get the point across to non-IT people.
I'm sure that has been mentioned before, but it's worth making sure that it's looked over and that while doing it you remember that when writing educative material, most people severely overshoot the level that they're aiming for, and end up writing a text that's perfect for undergrads when they were targeting a middle school audience or somesuch.
Personally, I'd leave in most of the random intercultural references (like the anime references, for instance) since I suspect they'd still reach a good portion of the audience and wouldn't have negative impact, but that'd be up for discussion. This also gives me an idea, but I'll make a separate comment for it.
However, there is some jargon that could and probably should be done away with: the computer science stuff.
On the one hand, I agree with you. If people can't understand, then that's bad. On the other hand, touches like those give the sequences personality, and that personality may be part of what makes them popular.
Usually, though, there's a way to phrase IT descriptions such that everyone can understand. I do this for my boss all the time. Maybe giving it a high-tech "personality" and making it comprehensible are not mutually exclusive.
As you may have heard, the Singularity Institute is in the process of creating an official ebook version of The Sequences (specifically, Eliezer's Major Sequences written between 2006 and 2009).
Now is an opportune time to make any alterations to the contents of the Sequences. We're looking for suggestions about:
Put separate suggestions in separate comments so that specific changes can be discussed. All suggestions will be reviewed, with final changes made by Eliezer. Next thing you know, you'll be sipping a hot mocha in your favorite chair while reading about Death Spirals on your handy e-reader.
The Sequences that will be present in the ebook: