Hopefully someone at Hashicorp can double check my read: I feel this could be compared to Skaffold or Tilt, but with a heavier emphasis on a plugin architecture. Is that right?
Yes, the plugin architecture is an essential part of Waypoint and we hope to see a large ecosystem of plugins. Rather than focuses exclusively on k8s, Waypoint is designed to center on the build, deploy, release workflow to any platform via plugins. There's a lot of plugins already built-in [1] and the Plugin SDK [2] makes it pretty straight-forward to build new ones.
[1] https://www.waypointproject.io/plugins [2] https://www.waypointproject.io/docs/extending-waypoint