Tax Optimization Engine

You are tracking write-offs in scattered notes, estimating quarterly payments from memory, and finding missing receipts the week your return is due. Each month, deductible expenses slip into personal spending, freelance income goes untiered, and you lose tax-loss windows you cannot reopen after year-end. Spreadsheets help for a week, then drift. Generic tax checklists fail because they do not recalculate as new income and expenses land. Tax Optimization Engine is a finance skill that turns ongoing tax prep into a repeatable operating system. It categorizes deductions, recalculates quarterly estimates from actual inflows, flags audit-risk expense patterns, and generates pre-filing evidence packets. It also runs depreciation timelines, charitable giving optimization scenarios, and tax-loss harvesting alerts using lot-level data. Named anti-pattern: it refuses "Receipt-Free Deduction Guessing" because unverifiable write-offs create audit exposure and false savings projections. What you get: SKILL.md — core operating protocol and decision rules. Quarterly-Estimate-Workflow.md — income-to-payment cadence with reminder triggers. Deduction-Category-Map.csv — IRS-aligned expense taxonomy. Freelance-Tax-Calculator.xlsx — self-employment and estimated-tax model. Depreciation-Schedule-Builder.xlsx — asset class timelines and deduction roll-forward. Tax-Loss-Harvest-Alerts.md — lot screening logic and execution guardrails. Pre-Filing-Checklist.md — final validation sequence. Dependencies: requires current tax-rate inputs, transaction exports, and calendar access for reminders.