Yeah, LL isn't set up for development so if things don't work well that way, I won't lose any sleep (everyone should know our mission statement by now). Normally. I wouldn't spend any time on this kind of request or just ignore it, but you have given so much to this community.
I've cut your quote down to - "Gems used to show up as gems. Scripts used to show up with the ruby app page icon, as did json. I'm sure I'll sort it out, but I think it may be linked to the LL base system dependency on vim tiny." The rest is unrelated hardware waffle.
I can't proceed until you send me some samples as first requested.