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Notes -
Dude, they're twice the median income for couples (119k vs 236k), and 2.5x the median income for singles (61k vs 150k).
I think you might be misunderstanding or misreading my question.
I'm not comparing making new Roth contributions to making new HSA contributions. I'm discussing the so-called “shoebox strategy” for how someone who has existing money in an HSA should treat existing HSA-eligible receipts that they don't have a burning need for reimbursement on—whether to hold on to the receipts without cashing them out to allow the money to grow in the HSA, vs other possible courses of action.
I've proposed a strategy that I think strictly beats the “shoebox strategy” in most cases, listed 2 edge cases where my proposed strategy doesn't beat it [namely: (a) someone who is not maxing out their Roth contributions and anticipates HSA exhaustion before age 60, and (b) someone who is already maxing out their Roth contributions and anticipates HSA exhaustion before death], and asked whether there are any other cases where my proposed strategy doesn't beat it.
In your example case, if those medical bills are so "significant" as to exceed 7.5% of your gross income, and your future self itemizes, my proposed strategy still beats the shoebox strategy, since while you still take the growth (on money your younger self did put into an HSA) out completely tax-free to pay the medical expenses, your future self doesn't thereby sacrifice the ability to get a that-year deduction for the medical expenses.
And even if they don't rise to that 7.5% threshold, or your future self doesn't bother to itemize, my proposed strategy leaves you no worse off than the shoebox strategy, since either way you're taking out completely tax-free growth (on money your younger self did put into an HSA) to pay for medical expenses.
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