With the one-time $300,000 annuity purchased at 65, at age 80 the retiree would have received total $2,050 monthly payments of $369,000.

If he had instead purchased (i) a single $100,000 annuity at age 65, he would have received $684 monthly payments totaling $123,120 at age 80. By additionally purchasing (ii) a second $100,000 annuity at age 70, he would have also received $775 monthly payments totaling $93,000 at age 80. Finally, by adding (iii) a third $100,000 annuity, purchased at age 75, at age 80, he would additionally received $909 monthly payments totaling $54,540. These these three annuities would have provided him a total of $270,660.

Assume that the retiree was able to the invest the dollar difference between the three laddered annuities and one-time $300,00 annuity at a fixed interest rate of 3% (i.e., the interest earned on $100,000 for 10 years at 3% plus the interest earned for 5 years at 3% = $50,319). Adding this to the $270,660 paid to him by the three annuities brings his total annuity payments and 3% fixed interest earnings to $320,979, or $48,021 less than the cummulative monthly income earned from the single $300,000 annuity.

Based upon the monthly difference between the amounts which he would have received between the single $300,000 annuity ($2,050) and three laddered annuity payments ($2,368) at age 80 and beyond, our retiree would have to reach an age of nealy 93 years before the laddered annuities payments surpassed the single annuity total.

Note that this analysis does not even address the fact that the retiree would have to have significant savings reserves available in order to offset the decreased annuity payments received during the initial years of his retirement.