I still wonder how come the first syntax was considered a good idea in the first place ?
Figuring how to configure webpack 1 (haven't tried 2) is crazy, and I don't understand how people able to construct such a complex tool that is currently unique on the market, and works so well, managed to design a conf settings that badly.
Ironically the biggest challenge is involved with connecting a very declarative under the hood plugin architecture, to a more imperitive fluid configuration for users. We would love all the great ideas we can get!