Hi! It sounds like you're trying to find the most tax efficient way to withdraw from your investment portfolio.
Generally speaking, if you sell investments that have appreciated significantly, you'll have a larger capital gain than if you sell things that have appreciated little or have gone down in value. So I would start by checking on the unrealized gains and losses on your portfolio - your broker should be able to provide this information. Depending on your basis and gains/losses, your taxable capital gain would be larger or smaller. To give an example, you said you want to withdraw a total of about $90,000. If you sold investments with a basis of $50,000 to get that withdrawal, you'd be paying taxes on $40,000 of gains ($90,000 sales proceeds - $50,000 basis = $40,000 gain). But if you sold different investments with a basis of $80,000, you would only have a $10,000 taxable capital gain.
Another idea, since we're getting towards the end of 2023: if you can split up the withdrawal across two tax years, you might be able to keep yourself in a lower tax bracket.
Take a look at this article and specifically, scroll down to the table that's labeled
2023 Long-Term Capital Gains Tax Rates
A Guide to the Capital Gains Tax Rate: Short-term vs. Long-term Capital Gains Taxes - TurboTax Tax T...
You can compare the info here for your filing status and your income to see if you can keep yourself in that 0% capital gains tax bracket by taking out part of the money this year and part next year. Paying a 0% capital gains rate would definitely be tax efficient! Keep in mind, the amounts in this table are your total taxable income from all sources, not just the capital gain amount. So it would include the part of your Social Security that's taxable, as well as any other taxable income you have from any other source.
Hope this information is helpful!
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