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<<Anyone have an example (using any numbers) of how you would ladder the above instruments to mature in 1-5 yrs so that you could roll the money in a MMF to use to supplement SS, and an annuity?>>

Simple. Say you have 10K. Divide by 5 to put 2k into each "basket". First basket matures in 1 year, second basket matures in 2 years, etc. At the end of the first year, withdraw the money you need and then (here's the trick) invest the "leftovers" from that basket to mature in 5 years. Do this each time a basket matures, invest for another 5 years.

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