> _When done well._ Every time I write an `if err != nil {}` block, I need to decide whether to return the error as is (`return err`) or decorate it with further context (`return fmt.Errorf("stuff broke: %w", err)`)

Easy. Always wrap. Wrap with what you were doing when the error occurred.

> I'm pretty sure logback's complexity is anathema to Go. But my goodness, it had some nice features... And then you just throw the stack trace in IntelliJ's "analyze stacktrace" box and you get clickable links to each line in every relevant file... I can dream.

Yeah, despite the proliferation of IDEs for Go in recent years, Go has traditionally been pretty anti- big-iron IDE.