The console logs the input that it sees when you having logging turned on like this; for that first one, did you pick the menu entry? The console should display no log output unless you pressed a key, so seeing #
seems a little off, unless you actually typed that key.
In addition to the input logging, you may also want to sublime.log_commands(True)
and then try again; that will show you not only what key Sublime thought you pressed, but also what command it’s trying to execute.
Lastly, it may be handy to ask what kind of file you’re trying to comment; what the command to toggle comments does depends on the type of file that you’re editing, and not all files support comments (for example Plain Text files do not), so you may be running into something in that area too.