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OBBB Tax Strategy & Preparation Checklist

1. Tax Planning & Documentation

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Schedule a proactive mid-year and year-end tax strategy session with a tax professional
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Update financial records to comply with OBBB documentation standards (digital and paperless encouraged)
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Review previous year’s returns for retroactive deductions introduced by OBBB

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2. Maximize New & Expanded Deductions

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Identify eligibility for expanded OBBB business deductions (e.g., equipment, Section 179, R&D expenses)

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Track and document new personal and business deductions: auto loans, business meals, childcare credits, etc.

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Integrate new payroll tracking for qualified tips and overtime, if applicable

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3. Optimize Credits & Phaseouts

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Confirm eligibility for new OBBB tax credits (childcare, paid leave, energy-related, etc.)

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Review phase-out thresholds by AGI and adjust withholding or income recognition accordingly

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4. Entity Structure & Compensation

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Re-evaluate business structure (S-corp, LLC, partnership) for OBBB tax efficiency

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Review owner/officer payroll and benefits to take advantage of new deduction or credit opportunities

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5. Recordkeeping & E-Filing Updates

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Digitize receipts and records for all major deductible expenses

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Confirm electronic filing compliance (required for 10+ returns issued)

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Update contractor/vendor information for new 1099 thresholds

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6. Retirement & Investment Planning

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Assess opportunities under OBBB for new retirement account deductions or limits
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Review investment sales for capital gains/losses with new OBBB holding period/regulations

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Integrate digital assets/crypto reporting if active

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7. Year-End Close & Preliminary Return Review

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Reconcile all bank, credit card, and payroll accounts

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Run a preliminary tax calculation for early warning of liabilities or refund estimates

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8. State & Local Updates

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Monitor for Florida and Tampa-specific OBBB conformity; adjust local filings as needed

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Action Steps:

  1. Share this checklist with your finance team or planner
  2. Book a complimentary OBBB readiness consultation with Guardian Accounting Group
  3. Set calendar reminders for key checkpoints in 2025 and 2026