Lets keep it real here, I do listen to my fav. song like 3-4 times a day and thats the limit. No matter how good the song it is, it does get boring after continuous listening. However, it sounds perfectly good if you listen to it after a break.
Once or twice. Just like with anything else, repeating runs the risk of you getting seriously annoyed.
Hah at least 40 times a day and after few days it isnt my favourite ong because i listened to it to much times