A big roadblock to getting both old (CHM veteran) and new people working on improving and expanding the highway data is the conversion to a new format. For the most part, as mentioned before, this is nearly trivial. My intent would be to convert all existing files, get them into their "official" location in GitHub and let people clone and fork and whatever else we decide is the way to manage the changes. The problem is that Tim's wptedit page would still use the old .wpt file format, with the OSM URLs. So the options as I see them:
1) We stick with the old format for now so we can keep using wptedit on Tim's site. We risk it disappearing, and are stuck with a file format that is a bit clunky but would work. But the process described above could happen almost immediately.
2) We copy and modify Tim's wptedit code (it's all available as far as I can tell) to use the new format. It should be nearly trivial to do, but I'm hesitant to take his code without his permission. I'm using some of his JS code in the map displays I developed but I had prior permission to use that code for my academic project, and a lot of it has been changed quite a bit since his last version so I feel like this is OK. In this case, we'd be making only small modifications, using most of his code as is, with no permission of any kind granted as far as I know.
3) Someone writes a brand new highway data file editor. This would take some time, I'm sure.