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I don’t understand the question.
Why would being retired affect how you transact in brokerage account?
For any brokerage account you track tax lots and have a cost basis for each lot. You can specific FIFO sales or pick specific lots. Doesn’t matter if it’s and ETF or individual stock.
Pro
You’ll pay taxes on the gains, so I’d look at whatever tax bracket you’re in and your current income levels. Early in retirement, maybe you’re still earning a bit of side money, so you have some extra income pushing you into a higher tier. I’d cash out your loss positions first to help minimize tax liability overall, and give any short-term positions time to become long term and reduce those taxes. As of right now, it’s a flat percentage of tax on all long term gains, so it really doesn’t matter when you cash those out.
Besides those tax considerations, I don’t know that there’s any reason to cash some positions before others.