Thank goodness I decided to bite the bullet last week and make the jump to v2. Upgrade took a while but was rather painless thanks to the great migration guide on the new documentation site.

If you are using a ton of loaders that aren't v2 ready you may have a more painful experience, you'll have to get familiar with the LoaderOptionsPlugin.

If you're newish to webpack it could be a frustrating experience.

Shout out to the webpack team though, It's an impressive tool.