Turns out, japanese's a really hard language. Like warakawa said, not really much in terms of tone differentiation to help one decipher so it's mainly a contextual thing. Sugoi I've been told is like the english word "awesome" and "awful" in one, so mainly it's something that makes an extreme of something (a situation can be "Awesome", "Terrific", "Great", or something can be "Awful", "Terrifying", "Great") Also, just a note about transliteration. sigoi = shigoi but sugoi = sugoi in the system you're using. Not really criticizing you just wanted to point it out to avoid future confusion.