The two key things I wish to briefly re-iterate: 1) after age 65, the HSA no longer has any restrictions (penalties) related to medical expenses, it works just

The two key things I wish to briefly re-iterate: 1) after age 65, the HSA no longer has any restrictions (penalties) related to medical expenses, it works just like a Trad. IRA except that if you do reimburse for medical expenses, the distributions are tax-free. 2) Each conversion from Trad. IRA to Roth IRA starts a five-year timer on that conversion, after which the amount converted can be withdrawn tax and penalty free, just like Roth contributions. So for example a 40-year old who leaves a job and rolls over a 401k balance to an IRA, can then choose to pay tax now (via Roth conversion) and then take out some or all the money penalty free at age 45, which is significantly younger than age 59.5 (for IRA) or 55-and-separated-from-service (for 401k).