This only works if you do not spend any of your HSA funds and instead invest them, paying for healthcare with post tax money.
In the ideal world, if I knew exactly when I’m going to die and how much I’m going to need to spend for healthcare every year - yes, I would totally do this to maximize the effectiveness of HSA.
However I don’t live in that world. It’s no use to me to spend my hard-earned post tax money and die having 100k in my HSA account. Maybe if I was making 200k+ a year to have enough to max out all tax-advantaged accounts AND cover medical expenses with post-tax dollars, sure, I would do it.
That’s why I spend my HSA money for medical expenses now. I’ve done the math and doing this it’s still costing me less than a PPO plan.
I think a better approach is to assume your costs can be anywhere from 0 to the max OOP and see how the numbers work out for different scenarios. Then you can make a decision based on financial (not health) risk tolerance
That’s exactly what I’m doing with the help of my spreadsheet.