Tax-Loss Harvesting Strategy

Prompt

Build a tax-loss harvesting strategy for my investment portfolio for [TAX YEAR].

Portfolio context:
- Account type: [TAXABLE BROKERAGE]
- Positions with unrealized losses: [LIST TICKERS AND APPROXIMATE LOSS AMOUNTS]
- Positions with large unrealized gains (at risk of harvest trigger): [LIST]
- Capital gains realized this year: [SHORT-TERM AMOUNT / LONG-TERM AMOUNT]
- Marginal tax rate: [PERCENTAGE]
- State tax consideration: [STATE AND RATE]
- Wash sale awareness: [YES I UNDERSTAND / NEED EXPLANATION]

Build the strategy:

1. **Harvest Candidate Analysis** — For each loss position: should I harvest? Analyze: loss amount, tax savings, wash sale risk, and whether the investment thesis still holds.

2. **Tax Savings Calculation** — Estimated federal and state tax savings from harvesting each candidate.

3. **Replacement Securities** — For each harvested position, suggest a replacement that:
   - Maintains my market exposure (avoids the wash sale rule)
   - Is substantially different from the sold security
   - Has similar risk/return characteristics
   - Includes a 31-day plan for potentially returning to the original security

4. **Wash Sale Rule Checklist** — For each harvest, verify: no purchase of the same security within 30 days before or after the sale.

5. **Year-End Timing** — When to execute each harvest to maximize this year's tax benefit.

6. **Long-Term Impact** — How does harvesting affect my cost basis and future tax liability?

7. **Action Plan** — Prioritized list of trades to execute with dates.