There's lots like that in the US, and to a much lesser extent in Europe as well. In the US I had a family member whose husband kept a not-great job because its insurance paid for her cancer treatment, whereas if he'd tried to switch jobs the other insurance might not have.

Even in Germany my (private) deductible is 3000 EUR so if I thought I might need "something done" I'd try to do it early in the year: if I spend 2999 in December the counter resets on January 1st. And I'm told I have a pretty sweet deal compared to America.

In the US, the first scenario is not a problem anymore since the Affordable Care Act requires coverage of pre existing conditions.

True, but I wouldn't place any bets on the longevity of the ACA until at least, say, mid-January.

It's actually a poor hint. You want to choose to be pregnant just before you elect your coverage for the following year. Then you can buy the gold plated care with a tiny out of pocket maximum. Then you can go back to a lower quality plan until you're ready for baby #2

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.