Biomedical and Electrical Engineer with interests in information theory, evolution, genetics, abstract mathematics, microbiology, big history, IndieWeb, mnemonics, and the entertainment industry including: finance, distribution, representation
Further to this and as a result of your post kinds session at IWC Austin, why not allow the user to personally write (or overwrite) the definitions of the UI readable parts so that they can create their own definitions of these things on their own sites. You can have placeholder text that a majority of people might agree with as a default, but by making it personally identify-able, you'll have solved part of your problem.)
Rob, you might notice at the top of that generations page it says, "Each generation is expected to lower barriers for adoption successively for the next generation."
I like your idea about de-jargoning some of the vocabulary and you even had a specific rewording. Why not use your site to log into the wiki and make that change manually, in the spirit of the quote at the top of the page? I have a feeling you'll get more praise than flack for trying to improve things. :)
With the help of Jeremy Cherfas and some others, we recently created the page for "cross-posting" and fleshed it out to help make the jargon jump between Gen1 and Gen2 a bit easier to handle.
I've found a lot of fun and value in subverting much of my Gen1 knowledge to help bridge things to the better angels of my Gen2 side. Better than writing mediocre code (in comparison to others), I find that I can have a more profound effect by helping Gen2 and Gen3 find their way based on what I've done. The bumps we find along the road also get reported back up the chain where those with more chops have been mightily swinging away to continually improve.
As for Homebrew Website Clubs or Camps, definitely try to attend one either in person or virtually regardless of your perceived level. (Austin is coming up next weekend!) I've seen folks like tantek, aaronpk, adactio and kevinmarks ever-so-kindly helping Gen4 people out to set up websites either in person or via chat!! It's definitely a site to see and is the rough equivalent of having Albert Einstein teaching you arithmetic, but it incrementally helps to make the world a nicer and kinder place, and definitely helps move the needle on the larger movement.
Do what you can and keep on hacking!
Between @BeakerBrowser and @IndieWebCamp, it looks like Austin is the place to be in December: