I hadn’t thought of that strategy! But my wife didn’t want to deal with brand new resident doctors, so avoiding the months of June onwards was important.

Also, I’m not sure if the out of pocket savings make up for the compounded investment earnings of a triple tax advantaged HSA contribution. However, it could work if both spouses get insurance from employer and they already have a kid, and the husband chooses an HDHP with HSA and puts one child under his insurance so he gets to contribute max amount to HSA, while wife chooses low deductible low out of pocket max plan and puts new baby under that.

But I wouldn’t waste my time figuring that out or doing that paperwork, it can’t be worth the different in out of pocket maximums and deductibles if you account for the headache of doing the paperwork.