CGO, for example, expects a comment immediately before a special import statement. A blank line between that comment and the import statement means that the comment is not attached to the import statement's AST node, and so is ignored. This confused me a fair amount when I started with CGO.
Part of the problem with comment syntax is that it's intentionally lexical and uniform. This simplicity means that you can easily obliterate the content of comments at any point in the input file stream via the tokenizer. However, Go instead has to bend over backwards in it's compiler toolchain to preserve comments beyond the lexer: in the parser, AST, code generator, etc.
Compare to docstrings in SmallTalk/Python/Clojure, where they are actual parsed string literals. Also compare to C#, which has explicit and distinct syntax for comments, metadata, and compiler directives. Comments can be inserted more or less anywhere. Metadata only where it's unambiguously attached to an AST node. And directives similarly to statements, unambiguously detached from other AST nodes.
With proper syntax for metadata, the CGO case would have been a compile time error about no AST node for the metadata to be attached to.
With proper syntax for directives, the //go:generate string-scanning bug would have never happened.
These syntaxes must be disjoint from comment syntax to eliminate the problems.