Of just those two I would choose option 1. You might want to instead consider the full single life annuity without the pop-up option if you could find life insurance at a better rate than the roughly 600 a month the pop-up option would cost you. What about SS for your DW the retiring teacher? I am thinking perhaps not so that she would definitely need either the pop-up option or some life insurance to cover it. BTW, congratulations you seem to be in great shape for early retirement unless your expenses are too high.