I'm a product manager working on Workers — didn't come across hater-y to me at all.
We will actually be rolling out a new version of our docs soon — hopefully make them easier to navigate, and expose deeper information. If there are any specific subjects or corner cases you've run into that you'd like to see better documented — our docs are open source (so issues are welcome!). We definitely want to make it as easy as possible for you to self-service.
Observability and debugging is also a heavy area of investment for us (and I think we've made significant progress here since the launch of Workers). As Kenton mentioned below, wrangler tail is a great way to get a lot of information out of the Worker (and its subrequests) — you can basically log anything. We'd also like to make it easier to log to existing logging platforms from a Worker. If there's any missing information you'd like to see, please do sent me a note ^