It's an interesting idea, but as a Devops Lead, I'm not sure this is any where near our biggest pain point. We've been in the midst of a Devops transition from manually managed EC2 and chef towards CI/CD and infrastructure as code for two years. Terraform solves one of our biggest problems - consistently representing infrastructure as code. But Waypoint won't solve the other. In fact, Waypoint doesn't seem to touch on anything that's actually much of a problem.
The deployment step isn't the problem - it's everything surrounding it. See, we're not on CI or CD yet. We're working our way towards them from a legacy system. In that intervening time, what we need is a generalized build tool that provides the ability to do CI or CD, but also allows you to just write general build and deployment pipelines that allow you to gradually automate that process and run them manually outside the context of an automatically triggered pipeline. We've been in this stage for two years, and the only tool that actually does this coherently is Jenkins. But Jenkins is an absolute nightmare to work with on many levels. Our only other real alternative would be to cobble together a mess of bash/python/nodejs scripts or use chat ops. There isn't a good solution in this space.
Gaia Pipeline, an open source project in development by a small team lead by a Hashicorp engineer, looks like it could be our long wished for Jenkins killer. I'd really love to hear your thoughts on whether Hashicorp might be willing to throw its full weight behind it: https://github.com/gaia-pipeline