Tax Loss Harvesting....

thank you everyone for the responses… I probably should have given more context. I am married filing jointly, our HHI with the standard deduction exceeds the 12% bracket. We have about ten years till FIRE. We are DCA monthly into our brokerage account (our largest account) and maxing out our retirement accounts. I am trying to see if there is a better way to optimize from a tax perspective from now till FIRE with our brokerage account.

Watch out for the wash sale rules. If you have been reinvesting dividends in what you are planning to sell, a portion of your loss could be disallowed for this tax year. 30 days before AND after the sale is the time period to be concerned about.

You might want to reconsider that and think about tax gain harvesting instead. If your income isn't too high (probably around $150k married or $75k single), then there is a good possibility that you are landing in the 12% tax bracket. If that is the case, then you are almost certainly best served by harvesting gains rather than (or in addition to) losses.

In essence, the 0% capital gains tax extends to (almost) the top of the 12% bracket. So, if you realize gains now and ask the government to tax you on it, then you are avoiding a 15% capital gains tax rather than a 12% marginal income tax. The nice thing about harvesting gains is that you don't have to concern yourself with the $3k limit (as the limit is actually dependent on how much room you have in the 12% bracket) and you also don't have the possibility of wash sales (especially if you still have money going into the market periodically, including dividend reinvestment) since wash sales only factor in when capturing losses.

White Coat Investor is a good resource for walkthroughs like this.

How to Tax-Loss Harvest at Vanguard [with Screenshots] | White Coat Investor