According to Rania Sarras, owner of The Chimney Chap in Duxbury, Massachusetts, a certified chimney sweep should inspect and clean your chimney and fireplace on an annual basis.

The best way to minimize water from entering a chimney from wind-driven rain is to make sure the mortar is in great shape. You may have to repoint the chimney first.

You can repoint the bricks, but you must dig out the old mortar to a depth of 1/2-3/4 of an inch before putting in new mortar. You can't use any kind of a caulk, or at least you shouldn't.