ComeOnOliver Tax Preparation
Help users organize and prepare for tax filing.
When to Use
- Organizing tax documents and receipts
- Creating tax preparation checklists
- Understanding common deductions and credits
- Tax timeline planning
- Estimating tax liability
When NOT to Use
- This is NOT tax advice. Consult a tax professional for your specific situation.
- Filing taxes (use tax software or a professional)
- Complex tax situations (business structures, international income, audits)
- State/provincial-specific rules without verification
⚠️ Important Disclaimer
This skill provides general tax organization guidance, NOT professional tax advice. Tax laws vary by country, state/province, and individual circumstances. Always consult a qualified tax professional for your specific situation.
Tax Document Checklist
Income Documents
- W-2 forms (from employers) — US / T4 slips — Canada
- 1099 forms (freelance, investment, interest income) — US / T5 — Canada
- K-1 forms (partnership/trust income)
- Social Security / pension statements
- Rental income records
- Sale of assets (stocks, property, crypto)
- Any other income documentation
Deduction Documents
- Mortgage interest statement (1098)
- Property tax receipts
- Charitable donation receipts
- Medical/dental expense receipts
- Student loan interest (1098-E)
- Tuition payments (1098-T)
- Business expenses (if self-employed)
- Home office measurements/expenses
- Vehicle mileage log (if business use)
- State/local taxes paid
Personal Information
- Social Security/SIN numbers (you + dependents)
- Prior year tax return
- Bank account info (for direct deposit/payment)
- ID for e-filing
Tax Organization System
Monthly Tracking
Keep a simple spreadsheet or folder system:
| Date | Category | Description | Amount | Receipt? |
|---|---|---|---|---|
| 1/15 | Medical | Dr. visit copay | $40 | ✅ |
| 1/20 | Charity | Red Cross donation | $100 | ✅ |
| 2/1 | Business | Software subscription | $29/mo | ✅ |
Category Organization
Create folders (physical or digital):
- Income — all income statements
- Housing — mortgage, property tax, insurance
- Medical — bills, insurance statements, receipts
- Charitable — donation receipts, acknowledgment letters
- Business — expenses, mileage, home office
- Education — tuition, student loans, books
- Investments — brokerage statements, buy/sell records
- Prior Returns — last 3-7 years of filed returns
Common Deductions Checklist
Often Overlooked Deductions
- Home office expenses (dedicated space for work)
- Professional development and education
- Job search expenses
- Moving expenses for work (limited)
- Charitable mileage (driving for volunteer work)
- Sales tax on major purchases
- Teacher classroom expenses
- Health Savings Account (HSA) contributions
- Self-employment tax deduction (50%)
Self-Employed / Freelancer Deductions
- Home office (square footage method or simplified)
- Internet and phone (business % only)
- Software and subscriptions
- Professional services (accountant, lawyer)
- Business insurance
- Travel for business
- Equipment and supplies- Home office deduction
Tax Calendar
| Date | Action |
|---|---|
| Jan 31 | W-2s and 1099s due |
| Apr 15 | Tax filing deadline |
| Jun 15 | Q2 estimated tax |
| Sep 15 | Q3 estimated tax |
| Jan 15 | Q4 estimated tax |