Tax Automation

Farm Vendors (Form F — 3553 Old Mission Rd)

• Agrivine — vineyard labor, pruning, harvest
• Manigold Orchards — cherry and pear tree maintenance, spraying
• Ginops — farm equipment rental and maintenance

Data Sources

• Gmail (gog CLI) — scan for tax-related emails (1099s, K-1s, property tax bills, vendor invoices)
• Google Sheets — Income Tax Tracking Items sheet (1Ua45Dw38A32RMo2L6IBc6NoC-hyQXGs4rZb_7uymLzg)
• Existing tax guides — 2025_Tax_Automation_Comprehensive_Guide.md in workspace
• Legacy scripts — scripts/legacy/ (see integration section below)

Quarterly ES Tax Reminders

Due dates for federal and CA/MI estimated tax payments:

• Q1: April 15
• Q2: June 15
• Q3: September 15
• Q4: January 15 (following year)

Reminder Workflow

1. Check memory/cron-state.json for last ES reminder sent.
2. If within 14 days of a due date, generate a reminder with:
   • Federal ES voucher amount (from prior year safe harbor or CPA estimate)
   • CA FTB 540-ES amount
   • MI MI-1040ES amount (if applicable based on MI rental/farm income)
3. Post reminder via email or Slack (see slack-teams-hub skill).
4. Update cron state after delivery.

Rental Income Tracking

Gmail Scan for Rental Deposits

import subprocess, json, re
from datetime import datetime, timedelta

def scan_rental_emails(days_back=30):
    """Scan Gmail for rental income notifications using gog CLI."""
    since = (datetime.now() - timedelta(days=days_back)).strftime("%Y/%m/%d")
    queries = [
        f"from:soper subject:rent after:{since}",           # Soper Services (3469 Old Mission)
        f"subject:rental payment subject:los altos after:{since}",  # 100 Main St
    ]
    results = []
    for q in queries:
        # Use gog CLI for Gmail search
        out = subprocess.run(
            ["gog", "gmail", "search", "--query", q, "--format", "json"],
            capture_output=True, text=True
        )
        if out.returncode == 0:
            messages = json.loads(out.stdout)
            for msg in messages:
                results.append({
                    "date": msg.get("date"),
                    "subject": msg.get("subject"),
                    "from": msg.get("from"),
                    "snippet": msg.get("snippet", ""),
                })
    return results

Update Google Sheet

def append_rental_to_sheet(property_name, amount, date, category="Rental Income"):
    """Append a rental income/expense row to the tax tracking sheet."""
    sheet_id = "1Ua45Dw38A32RMo2L6IBc6NoC-hyQXGs4rZb_7uymLzg"
    row_data = f"{date},{property_name},{category},{amount}"
    subprocess.run([
        "gog", "sheets", "append", "--spreadsheet-id", sheet_id,
        "--range", "Transactions!A:D", "--values", row_data
    ], check=True)

Form F Agricultural Deductions (3553 Old Mission Rd)

Track expenses by vendor for Michigan Form F (Schedule of Farm Income/Loss):

• Labor: Agrivine invoices for vineyard work
• Supplies & maintenance: Manigold Orchards for orchard care
• Equipment: Ginops invoices for equipment rental
• Property taxes: Traverse City property tax on agricultural parcels
• Insurance: Farm liability and crop insurance

Vendor Invoice Scan

FARM_VENDORS = ["agrivine", "manigold", "ginops"]

def scan_farm_invoices(year=2026):
    """Scan Gmail for farm vendor invoices."""
    results = []
    for vendor in FARM_VENDORS:
        out = subprocess.run(
            ["gog", "gmail", "search", "--query",
             f"from:{vendor} OR subject:{vendor} after:{year}/01/01 before:{year}/12/31",
             "--format", "json"],
            capture_output=True, text=True
        )
        if out.returncode == 0:
            messages = json.loads(out.stdout)
            for msg in messages:
                results.append({"vendor": vendor, "date": msg.get("date"), "subject": msg.get("subject")})
    return results

Depreciation Schedules

Rental properties use straight-line depreciation over 27.5 years (residential):

• 3469 Old Mission Rd — basis, placed-in-service date, annual deduction
• 100 Main St, Los Altos — basis, placed-in-service date, annual deduction

Track in the Google Sheet under a "Depreciation" tab. Update annually or when capital improvements are made.

Workflow

1. Daily/weekly scan: Run Gmail scan for new tax-related emails (rental payments, vendor invoices, 1099s).
2. Categorize: Match emails to property and expense category.
3. Record: Append to Google Sheet tax tracking spreadsheet.
4. Quarterly: 14 days before ES due date, generate payment reminder with amounts.
5. Year-end: Compile Form F totals, rental P&L by property, depreciation schedules for CPA.

Error Handling

• Gmail auth failure: Re-authenticate with gog auth login — see skills/google-oauth-reauth/SKILL.md.
• Sheet write failure: Check sheet permissions; Eric must share with the service account.
• Missing vendor emails: Some vendors mail paper invoices — flag for manual entry.
• Multi-state complexity: CA and MI have different rules; flag anything unusual for CPA review.

Integration Points

• Legacy scripts (scripts/legacy/):
  • subscription_tracker.py — subscription cost tracking (overlaps with expense categorization)
  • tax_email_scan.py, check-tax-emails.py, scan-tax-emails.py — prior Gmail scanning implementations; reference for query patterns but use the workflow above for new runs
  • add-tax-emails-to-sheet.py — prior sheet integration; patterns reusable
  • create_farm_tax_doc.py — Form F document generation
• Google Sheets (subscription_tracker.py writes to the same subscription sheet)
• Daily briefing: Tax reminders can be included in the daily CFO briefing when ES dates approach.
• Incident logging: All failures logged to memory/incidents.jsonl.