It's kind of funny, since past few days I have been mostly configuring Webpack 2 builds. The #1 most difficult part for me was to setup loaders to correctly process static assets. E.g. I had problems with style-loader and external fonts (where I've found a very specific race-condition-ish case where it just didn't work). Also, I think the documentation for some (even contrib) loaders should be more verbose, including examples for both inline and external config.
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