This should be feasible either with gulp or by running jekyll b --watch and then running browsersync in the _site directory (probably the easiest).
Other option (better option) is to make a node server with sockets.io which controls both the cli and the dashboard. This is a long-term goal and has little current advantages over the large overhead.
If you know how to do that, you can leave resources here and look at how you can help.
Things to take in account
- deployable fast on multiple computers
- deployable without internet connection
- deployable on computers that didn't have node yet