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Notes -
It seems to me that occasional (over years or decades) medical expenses between the ages of 21 and 60 is a pretty realistic projection. In which case, why not have the money somewhere where it can both generate wealth and be spent tax-free?
This is such a vague sentence I don't understand it. What, exactly, are you saying? (Both the shoebox strategy and my proposed strategy allow the money to continue growing, and the growth on that money to eventually be spent on medical things without incurring any capital gains or other taxes — but, unlike the shoebox strategy, my proposed strategy doesn't ruin your future self's ability to deduct those expenses when those expenses exceed 7.5% of your gross income, and my strategy additionally allows the gains to still be completely tax-free in the happy-albeit-unlikely event that you don't spend them all on medical expenses before death.)
Are you claiming that the shoebox strategy ever beats my proposed strategy for someone who doesn't anticipate HSA exhaustion before age 60? If so, please explain.
Keep in mind, the shoebox strategy (which is what I'm rebutting) only applies when someone has incurred a medical expense, doesn't particularly need reimbursement at the moment, but has the money already in their HSA such that they could take reimbursement.
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