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Sample Questions for Poolula LLC Assistant

This document contains sample questions organized by persona and topic area. These questions demonstrate the types of queries the assistant can answer using the RAG system (database queries + document search).

1. New LLC Owner (Compliance & Getting Started)

Formation & Structure

  1. What documents do I need to maintain for my LLC?
  2. How do I complete my first year of LLC compliance requirements?
  3. When are my important LLC deadlines and filing dates?
  4. What is the business purpose of Poolula LLC according to our formation documents?
  5. Who are the members and managers of Poolula LLC?
  6. What is our LLC's EIN (Employer Identification Number)?
  7. When was Poolula LLC officially formed?
  8. What state is Poolula LLC registered in?
  9. What are the key provisions in our operating agreement?
  10. How is Poolula LLC taxed (partnership, S-corp, etc.)?

Annual Compliance

  1. When is the Colorado periodic report due?
  2. What's required for the Colorado periodic report filing?
  3. What annual compliance items do we need to complete?
  4. Do we need to hold annual LLC meetings?
  5. What records do we need to keep for annual meetings?

Basic Operations

  1. What bank account does Poolula LLC use?
  2. Who has signing authority for the LLC?
  3. What insurance policies does Poolula LLC have?
  4. Where are our LLC documents stored?
  5. What is the LLC binder organization structure?

2. Bookkeeper (Financial Records & Accounting)

Property Basis & Depreciation

  1. What's the current tax basis of our property and assets?
  2. What depreciation schedule should I use for our rental property?
  3. What is the land basis for our property at 900 S 9th St?
  4. What is the building basis for our property?
  5. What is the FF&E (furniture, fixtures & equipment) basis?
  6. When was our property placed in service?
  7. What is the total depreciable basis for our rental property?
  8. What depreciation method should we use (MACRS, straight-line)?
  9. What is the useful life for our building depreciation?

Transaction Analysis

  1. What was my rental income in August 2025?
  2. What were total expenses in 2024?
  3. Show me all utility expenses for 2024
  4. What property management fees did we pay last year?
  5. How much did we spend on repairs and maintenance in 2024?
  6. What were our property tax payments in 2024?
  7. List all transactions for property ID [uuid]
  8. What were the largest expenses last quarter?
  9. Show me transactions between January 1 and March 31, 2025
  10. What categories of expenses do we have?

Revenue & Income

  1. What was our gross rental income for 2024?
  2. How many Airbnb reservations did we have in November 2024?
  3. What was the average nightly rate for our rentals?
  4. What service fees did Airbnb charge us last month?
  5. What was our occupancy rate last quarter?
  6. Compare revenue from Q3 2024 vs Q4 2024

Accounting Records

  1. Show me all accounting records and financial documents for 2024
  2. What accounting system or method do we use?
  3. What accounting notes or procedures are documented?
  4. Are we using cash or accrual accounting?
  5. What financial statements do we generate?

3. Property Manager (Operations & Maintenance)

Property Information

  1. What properties does Poolula LLC own?
  2. What is the address of our rental property?
  3. When did we acquire the property at 900 S 9th St?
  4. What was the purchase price of our property?
  5. What is the property's current status (active, sold, etc.)?

Leases & Tenants

  1. What are the current lease terms and key dates for our property?
  2. Do we have any active leases on file?
  3. What are the important dates in our lease agreements?
  4. What are tenant responsibilities according to the lease?
  5. What are landlord responsibilities according to the lease?

Insurance & Risk Management

  1. What insurance coverage do we have and when does it renew?
  2. Who is our insurance provider?
  3. What is our insurance policy number?
  4. What is covered under our property insurance?
  5. What is the deductible on our insurance policy?
  6. When does our insurance renew?
  7. What is the insurance coverage amount?

Vendors & Maintenance

  1. Who should I contact for property maintenance and vendor services?
  2. Do we have any vendor contracts on file?
  3. What property management companies have we worked with?
  4. Who handles lawn care or landscaping?
  5. Do we have any recurring maintenance agreements?

Colorado State Compliance

  1. When is the next Colorado periodic report due and what's required?
  2. Are we compliant with all Colorado LLC requirements?
  3. What state filings do we need to make this year?
  4. What is our Colorado entity ID or registration number?
  5. Have we filed all required Colorado reports?

Tax Compliance

  1. What tax filings and compliance items are due this quarter?
  2. When are federal tax returns due for our LLC?
  3. What IRS forms do we need to file (1065, Schedule E, etc.)?
  4. Have we filed for any tax extensions?
  5. What tax deadlines are coming up?

Compliance Status & Documentation

  1. Are we compliant with all LLC requirements and regulations?
  2. What compliance documents do we have on file?
  3. Do we have all required licenses and permits?
  4. What regulatory requirements apply to our rental property?
  5. What compliance checklists or procedures do we follow?

5. Tax Planning & Strategy

Tax Deductions & Credits

  1. What expenses are tax-deductible for our rental property?
  2. Can we deduct property management fees?
  3. How do we deduct mortgage interest for rental property?
  4. What are the rules for deducting repairs vs. capital improvements?
  5. Can we take a home office deduction?

Tax Forms & Reporting

  1. What information do I need for Schedule E (Supplemental Income)?
  2. How do we report rental income on our tax return?
  3. What is a K-1 and do we issue them?
  4. Do we need to file Form 1065 (Partnership Return)?
  5. What tax forms did we file last year?

6. Document Search & Retrieval

Finding Specific Documents

  1. Show me all formation documents
  2. Where is our operating agreement?
  3. Find our EIN assignment letter
  4. Show me all insurance documents
  5. Where are our tax documents stored?
  6. List all documents in the LLC binder

Document Content Search

  1. What does our operating agreement say about member distributions?
  2. Search for information about annual meeting requirements
  3. Find all references to "trustee" in our documents
  4. What do our formation documents say about business purpose?
  5. Search for insurance coverage details in our policies

7. Data Analysis & Reporting

Financial Summaries

  1. Summarize all revenue and expenses for 2024
  2. What is our net operating income (NOI) for the property?
  3. Calculate cash flow for last quarter
  4. What is our return on investment (ROI)?
  5. Compare expenses year-over-year (2024 vs 2025)

Transaction Grouping

  1. Group transactions by category for 2024
  2. Show transactions grouped by month
  3. Aggregate all utility expenses
  4. Total all revenue transactions for Q4 2024
  1. What are our top 5 expense categories?
  2. How have utility costs trended over the past year?
  3. What months have the highest revenue?
  4. Are there any unusual or irregular transactions?

8. Multi-Step & Complex Queries

  1. What was our rental income in August 2025 and what does our tax guide say about reporting it?
  2. Show me repair expenses for 2024 and explain which are deductible
  3. List all compliance deadlines and show me the relevant compliance documents
  4. What insurance do we have and when did we last review our coverage according to meeting minutes?

Cross-Reference Questions

  1. Compare our actual expenses to budgeted amounts in our accounting notes
  2. Verify that all transactions have proper documentation
  3. Check if we've met all compliance requirements listed in our checklist
  4. Reconcile Airbnb deposits with rental income transactions

Planning & Decision Support

  1. What tax planning strategies are mentioned in our accounting notes?
  2. Based on last year's expenses, what should we budget for utilities?
  3. What capital improvements have we made and how do they affect our basis?
  4. Review our compliance status and identify any missing items

Question Categories Summary

  • Formation & Governance: 1-20
  • Financial & Accounting: 21-50
  • Property Operations: 51-72
  • Compliance & Legal: 73-87
  • Tax Planning: 88-97
  • Document Management: 98-108
  • Analysis & Reporting: 109-121
  • Complex Queries: 122-133

Total Questions: 133

Using These Questions

For Testing

  • Use these questions to test the evaluation harness
  • Add expected answers to create golden question sets
  • Verify tool usage (database query vs document search)
  • Check citation accuracy and source tracking

For Development

  • Identify gaps in database schema or document coverage
  • Improve prompt engineering for specific question types
  • Train users on what types of questions work well
  • Develop new features based on common question patterns

For Users

  • Copy questions from appropriate persona section
  • Modify questions with your specific property details
  • Combine multiple questions for comprehensive analysis
  • Use as templates for creating custom queries

Last Updated: 2024-12-10 Document Status: Initial Version - Will expand with real query results