I think I've finally got a simplified plan that will work...
Age 44 - single
1.1 M outside IRAs
225k inside IRAs
So I dollar value average 1 M into Vanguard's new managed payout fund (available early next year) over the next 3 years - the 5% payout option. I'll live on maturing CDs in the intervening 3 years.
That should generate something on the order of 50k per year once established.
Of that 50k, I figure taxes should be something like 7k per year, assuming that the managed payout funds distributions are 1/2 capital gains and 1/2 interest payments.
So the expected "spendable" money becomes 50 - 7 - 3 (HSA contribution) = 40k /year, 3.3k/mo.
I only spend about 2k/mo now.
The IRA money would be left untouched, and total portfolio withdrawal would only be 3.6% (since the HSA contribution is not really spending, its just a transfer from one account to another).
If there is money left at the end of the year, I would transfer that into my Roth IRA, possibly lowering the withdrawal % further.
I have an individual Anthem HSA with a $2500 deductible - costs me $156/mo. (Just went up from $147 - only a 6% increase. Colorado is thinking about implementing mandatory health care, sort of in the model of MA, so I assume the insurance companies are playing nice until they get a chance to shoot it down
The IRA money would become available in 16 years, SS in 18 years.
Seems workable. Am I missing anything?