For example, am I going to do something major like have a baby this year. Then yes it probably makes more sense to get me to my deductible and pay the extra money to go with insurance. Or if you (or someone on your plan) has an ongoing medical issue where you know you will meet your deductible. Or on the flip side, I met my deductible one year and was going to physical therapy. Since I met my deductible the physical therapy visits were cheap, but going in to the next calendar year now my deductible reset. Could I have used more PT? Maybe, but the visits were about to be 5x more expensive.
But "expected medical expenses" is just the dumbest thing.
But we have to pay the bills after the insurance company does the calculation, which often results in annoying surprises.
The better your insurance, the less nasty surprises, which largely in the US means "the better you're paid, the less you have to pay out of pocket for health expenses" which is a nasty thing because then the people most likely to be hit with a big bill are those who can least afford it.