Two readings, two different words. This one is kànhǎo, built on 看 to look at, and it rates something's chances highly. Read kānhǎo, with 看 meaning to guard, the same two characters tell you to keep a close eye on someone or something.
usage
Business and sports writing lean on it: you 看好 a stock, a market or a team when you expect it to come out on top. The negative 不看好 is just as frequent and is the measured way to say something looks doomed.
