Comprehensive CPA Interview Questionnaire for Real Estate Investors

Introduction Script

“Thank you for your time today. I am a real estate investor seeking a strategic tax partner, not just a tax preparer. I’m looking for someone who can provide proactive guidance throughout the year to help optimize my tax position while ensuring compliance. This conversation will help me understand your expertise and approach to serving clients with complex real estate portfolios.”

I. Core Real Estate and Corporate Tax Expertise

1. Real Estate Tax Experience
   “Could you describe your experience with real estate investor clients? What are the most common advanced tax strategies you help them implement, such as cost segregation studies, bonus depreciation, or navigating real estate professional status requirements?”

2. Entity Structure Knowledge
   “What is your experience advising on the tax implications of different entity structures for real estate holdings, including LLCs, S-Corps, and partnerships? How do you determine the optimal structure for various scenarios?”

3. Complex Ownership Structures
   “Have you assisted clients with advanced ownership structures like series LLCs, holding companies, or complex partnership agreements? Can you walk me through a representative scenario?”

II. Role as a Proactive Tax Strategist

4. Strategic Approach
   “My philosophy is that tax planning is a year-round activity. How do you function as a strategic advisor to legally minimize tax liability, rather than just preparing annual returns?”

5. Planning Process
   “What does your typical tax planning process look like? Do you offer proactive quarterly or semi-annual reviews to model scenarios and advise on strategies before implementation?”

6. Proven Results
   “Can you provide a specific example of advice you gave that significantly reduced a client’s tax burden through proactive planning, rather than just through annual return preparation?”

III. Service, Experience, and Logistics

7. Relevant Client Base
   “What percentage of your current client base consists of real estate investors or real estate businesses? Can you provide approximate numbers?”

8. Collaboration Approach
   “How do you typically collaborate with clients’ attorneys on entity formation or complex transactions? Do you have a network of real estate attorneys you work with regularly?”

9. Fee Structure
   “What is your fee structure for ongoing advisory services? Is it retainer-based, hourly, or bundled with compliance work?”

IV. Private Lending Expertise

10. Private Lending Experience
    “What experience do you have with clients who act as private lenders? How do you handle the tax treatment of points, origination fees, and interest income, particularly when loans are structured through entities?”

11. Default Scenarios
    “How do you advise clients on handling non-performing or defaulted loans? What are the specific requirements for documenting and claiming a bad debt deduction?”

12. Entity Strategy for Lending
    “What are the advantages and pitfalls of using different entity structures (C-Corporations vs. pass-through entities) for a client building a portfolio of private mortgages?”

V. Self-Directed IRA Real Estate Investments

13. SDIRA Experience
    “Have you directly advised clients on tax compliance for Self-Directed IRAs investing in real estate? What has that experience involved?”

14. Prohibited Transactions & UBIT
    “Can you explain common prohibited transaction pitfalls and how UBIT (Unrelated Business Income Tax) applies to leveraged real estate in SDIRAs?”

15. Coordination Process
    “How do you coordinate with SDIRA custodians and other advisors to ensure proper transaction structuring and reporting?”

VI. Creative Financing & Advanced Structuring

16. Creative Financing Tax Treatment
    “What is your experience with the tax treatment of ‘Subject-To’ financing, seller-financed transactions, and installment sales? How do you handle imputed interest rules and basis calculations?”

17. Hybrid Transactions
    “How do you approach tax reporting for hybrid transactions like wrap-around mortgages (AITDs) and lease options? When do option payments get treated as rent versus purchase deposits?”

18. IRS Recharacterization Defense
    “What is your approach to documenting creative deals to ensure they withstand IRS scrutiny and aren’t recharacterized?”

19. Land Trust Taxation
    “How do you handle tax reporting for properties held in land trusts? What are the key filing requirements and elections?”

20. Risk Assessment
    “In your view, what is the single biggest tax pitfall for investors using advanced creative financing strategies, and how do you help clients avoid it?”

VII. Client Relationship & Communication

21. Communication Style
    “What is your typical communication protocol? How quickly do you respond to urgent questions, and what is your preferred method of communication?”

22. Client Onboarding
    “What does your client onboarding process look like? What information do you need from me to provide comprehensive advice?”

23. Technology & Tools
    “What technology platforms do you use for client collaboration, document sharing, and financial analysis?”

24. Specialization Commitment
    “How do you stay current with the constantly changing tax laws affecting real estate investors?”

25. Client Success Metrics
    “How do you measure success for your real estate investor clients beyond just tax savings?”

Closing Question

“Based on our discussion today, do you have any concerns about your ability to handle my specific situation? Is there anything about my strategy or approach that raises red flags from a compliance perspective?”

Evaluation Scoring Sheet

Rate each section 1-5 (1=Poor, 5=Excellent)

Red Flag Checklist

• □ Unable to provide specific examples

• □ Dismissive of advanced strategies

• □ Vague about fees or process

• □ Unfamiliar with key terminology

• □ No real estate-specific clients

• □ Defensive about questions

• □ Poor communication during interview

• □ Cannot explain UBIT/prohibited transactions

• □ No collaborative attorney network

• □ Focused only on compliance, not planning

Perfect candidate will:

• Ask thoughtful questions about your goals

• Provide clear, specific examples

• Demonstrate curiosity about your strategy

• Explain complex concepts clearly

• Show awareness of both opportunities and risks

• Emphasize documentation and compliance

• Discuss being part of your professional team

Use this comprehensive questionnaire to identify a CPA who can not only handle compliance but also serve as a true strategic partner in building and protecting your real estate wealth.