If you mean you yourself, then whenever you feel like it.
If you’re administering a mail server for other users, then you probably want to take other opinions into account.
If you want actual data to help make a decision, maybe you could take all the hotmail addresses from your addressbook and see how many of them are still valid and get a response.
(I've only got 20 in my addressbook and most of them are old, but one is my sister. In fact, I had to decrease the score of a Hotmail-specific SpamAssassin score in order to see mail from her.)
no subject
If you’re administering a mail server for other users, then you probably want to take other opinions into account.
If you want actual data to help make a decision, maybe you could take all the hotmail addresses from your addressbook and see how many of them are still valid and get a response.
(I've only got 20 in my addressbook and most of them are old, but one is my sister. In fact, I had to decrease the score of a Hotmail-specific SpamAssassin score in order to see mail from her.)