One solution to the pain of installing plugins is to move to a two container configuration. This let’s you build and rebuild new containers while your old one merrily continues.
I’ve mostly written a discourse-setup that will do a two container install. That keeps the site from going down in a rebuild and means that if it fails you can figure out the problem without the pressure of a broken site.
I’ve not quite completed it because I actually have enough work now that I’m not looking for projects. Also, the implications of supporting another configuration seem daunting. Will people know that instead of “rebuild app” they will “rebuild web”? Do we change and make this the default configuration? What about all of the old ones with a single container?
I’ve not been so successful in making the transition from one to two container configurations seemless, though a simple backup and restore isn’t that difficult to do manually.