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I'm sorry for the length of this post. I'll appreciate anything you care to comment on.

When you talk about Social security, I assume you're talking about receiving social security. That can become a bit messy, as the amount of your social security that is taxable will depend on how much other income you are reporting. At certain points, adding $100 of additional income will also make another $85 of your social security taxable. That is effectively almost doubling your tax rate. So there's a bit of slipperiness in things here.

My suggestion would be to stop being overly cost conscious, and spring for the tax software. Or better yet, take your figures to your tax preparer and pay for a bit of professional advice. A good tax pro will have the planning tools to help you reach the goal you're looking for. And you do have a good general plan, but I think it will take some professional assistance to get you there.

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