To me, Roof with a Hole is about people in general. Sometimes people have a tendancy to lose their sense of self, either through relationships, or through any natural event. Hence, a roof with a hole, is about your sense of self, and the rain coming in is whatever issues or problems you are trying to deal with at the time. When you have a "roof with a hole" the problems seep in and wash away your sense of self. The second verse applies to trying to get people to realize that it happens to everyone, not just people who have nothing. You could be rich beyond your wildest dreams and still lose your sense of self. Hence, "there may be diamonds in that dream on the hill". The third verse is about, how difficult it is to get a grip of reality and common sense once those problems are coming through and washing away who you once knew to be you. The song is meant to put to words those feelings, thoughts, and sensations.
To me, Roof with a Hole is about people in general. Sometimes people have a tendancy to lose their sense of self, either through relationships, or through any natural event. Hence, a roof with a hole, is about your sense of self, and the rain coming in is whatever issues or problems you are trying to deal with at the time. When you have a "roof with a hole" the problems seep in and wash away your sense of self. The second verse applies to trying to get people to realize that it happens to everyone, not just people who have nothing. You could be rich beyond your wildest dreams and still lose your sense of self. Hence, "there may be diamonds in that dream on the hill". The third verse is about, how difficult it is to get a grip of reality and common sense once those problems are coming through and washing away who you once knew to be you. The song is meant to put to words those feelings, thoughts, and sensations.