Food, if it looks fine and smells fine, no bulging cans or broken seals on jars, I'll give it a quick taste test. If all senses say it's fine, I'll go ahead and eat it. Best By dates are mainly indicators of freshness, not safety. Use By dates can go either way, but are generally quite conservative, and most things last longer if stored properly.
Medications, depends what's in it. Solid dose/tablet or capsule products stay good for a long time, though may lose some efficacy. With very stable compounds (Ibuprofen, for instance), the expiration date is more about how long it's worth testing out to, rather than something actually being wrong with the product. In my experience, most companies won't bother testing past 3-4 years max, but if a product is meeting criteria at 4 years, there's no reason to expect it won't make it to 5. Gel capsules I'm more suspicious of, especially if they weren't stored perfectly - and the medicine cabinet in a bathroom is a terrible place to store medications. Liquid dosage products are even more iffy, and especially anything containing Phenylephrine. Those I wouldn't take much past expiry. Anything with a 2 year rather than a 3 year expiration period, it's probably because in testing some parameter was trending toward failing criteria. Throw away and buy a new one.
Things like lotion and makeup, the main concern is the potential for bacterial growth. Pump bottles are safer than flip top bottles are safer than jars you stick your fingers in.
Sunscreen came up in another thread - definitely loses efficacy, but I still use out of date sunscreen. That calculation might change if I burned easily, had a family history of skin cancer, or spent a lot of time outside.