How much is his projected annual expense? Let's assume it is 250K.
He basically has 3 types of choices:
1) Buy annunity;
2) Buy real estates
a) Rental properties;
b) Private (non tradable) REIT which may yield at 6+%;
3) Buy balanced fund with income stream
Put 250K*2 aside as for the first 2 years expense. Buy conservative balanced fund with income stream (e.g: PAUIX yield +6% or VWINX yield +3%) using DCA to take positions in 12 month timeframe. Keep 1 year expense in cash as buffer. Use extra cash flow from dividends to buy more mutual fund shares or invest in funds with growth through an economic cycle(e.g: SGIIX, PRPFX).
Since current interests are low, 1) and 2b) may not give him attractive rates as they are expected to rise.