Pay medical bills out-of-pocket, keep receipts forever, reimburse yourself from HSA years later — tax-free.
No time limit exists between incurring a qualified medical expense and reimbursing from an HSA (as long as the expense was after the HSA opened and not otherwise reimbursed/deducted). Strategy: contribute max to HSA ($4,150 single / $8,300 family 2024), invest aggressively, pay medical bills from taxable cash, and STORE receipts. Decades later, withdraw tax-free reimbursements as needed. HSA grew tax-free the whole time. Combined with §223(a) triple-tax advantage: deductible in, tax-free growth, tax-free out. Ultimate stealth Roth.
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Multiply the $10M §1202 exclusion across multiple trusts.
4% corporate tax + 0% capital gains for bona fide residents.
Stack the $500K primary-home exclusion on top of a 1031 deferral.
Convert Traditional to Roth during sabbaticals or business-loss years.
Capitalize property taxes and interest on undeveloped land.
Deduct now, control forever, employ heirs.
Ordinary loss (not capital loss) on failed small biz — up to $100K.
Buy leveraged real estate inside your IRA — tax-deferred or tax-free.