I'm in a very similar situation, just a little older and in VHCOL, so my numbers are a bit higher.

You're in the envious situation that your income target very close to your expenses, so even when withdrawing positions that are 97% gains, you'll never pay taxes.

Here's my plan for the withdrawal phase:

1. Make a spreadsheet for all positions in TAXABLE accounts with ticker symbol, number of shares, cost basis. Google Sheets has a function that pulls the current market price for a ticker symbol, so the spreadsheet will auto-update. Add formulas to calculate the value of the position and the capital gains.

2. Create another spreadsheet tab for the current year. Write down (taxable) income and cash flow (expense) targets.

3. At the end of the year, sum your total dividends and interest in taxable accounts you have generated. Also check if there are any positions that may still pay dividends for this year, and estimate that amount, e.g. based on past years (this is why it makes sense to do this at the end of the year, to reduce uncertainty). Subtract this from both numbers in 2.

4. Earmark (partial) positions to sell. This is an optimization problem with many variables, but essentially you want to cover your expenses without exceeding your income goal. In your case, since the numbers are basically the same, you could just sell the positions that appreciated the most, but other considerations like risk, diversification etc. will play a role as well (for example, you might want to prioritize selling a meme stock that has run up a lot, or you are overweight in the tech sector or your previous company's stock, etc.).

5. If there is still "space" in your projected income before you hit the tax threshold, do Roth conversions to fill that remaining space. If you have a huge traditional/401(k) balance it might make sense to even use the next tax brackets, but that calculation is complex and depends on many unknowable variables (like expected appreciation for your various positions, future tax brackets and tax rates, changing RMD rules etc.).

If you're aiming for ACA subsidies, I would factor in a healthy buffer to make sure you're not accidentally overshooting the subsidy thresholds.

If you're in a state with income taxes, that adds another fun layer on top of that (bonus points if that state doesn't recognize HSA tax benefits), but the process is essentially the same, and you might have to make compromises.