Insurance. It’s complicated and confusing, which is why many people end up with insurance they don’t need, while neglecting to carry the type of basic insurance they do need. So how are we to know?

Dear Cheapskate: After 10 years at the same job, my husband was recently laid off. I’m a freelance writer. I work mainly from home so I can be with our 3-year-old son. We’ve always relied on my ...