Re 2: I love the idea of automating, but it rarely seems to pay off, because you really need a large number of users for it to be worth the effort to finish it/polish it properly - ease of use, ease of deployment, docs, helpful error messages, samples etc. All the things Fred Brooks talks about for a "programming product". https://wikipedia.org/wiki/The_Mythical_Man-Month

That's why we have products (including open source tools).