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So, my hope is to narrow down some choices, give myself time to investigate, then sit back and watch what happens to those potential choices. From this money, we need to replace income of $475/mo.

$475/mo. on $165K is a bit less than 3.5% return. You can get a good bit higher than this today in CDs. PenFed is paying 4.5% on 5-year CDs, so you would get the income you need plus an extra $143.75/mo. (minus taxes) to add to your savings. It would take 6 years of 5% inflation for your monthly needs to reach what you will get from the PenFed CDs should rates remain where they currently are.

Getting the income you need does not seem to be a significant problem to me. Of course, rates could fall between now and when the money matures. I don't think this is likely, but you never know...

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