Exams of high net worth individuals are conducted by the IRS Global High Wealth Industry Group, which is made up of experienced IRS auditors and forensic accountants. They commonly start with examining an individual and spread to that individual’s related entities, including partnerships and S or C corporations. Exams conducted by the Global High Wealth Industry Group can last from 18 months to two years.
The following are common items that the IRS examines, as well as suggestions for how to document and support the activity reported on the tax return:
Sale of partnership interest
IRS scrutiny is high particularly when significant gains are involved. Agents typically request various executed documents, including:
- Partnership agreements
- Purchase/sale agreements
- Promissory notes
- Appraisals
- Tax basis calculations
- Documentation supporting characterization of the gain (e.g., distinguishing between ordinary income and capital gain)
Additionally, the IRS may inquire about the section 754 election, which allows for a step-up in basis. It is crucial to indefinitely retain copies of any elections filed with the IRS because they can be essential for compliance and future reference.
Large gains transactions
It’s essential to have comprehensive documentation to support significant gains. Agents typically request various executed documents, including:
- Sale agreements
- Promissory/installment notes
- Detailed gain calculations
- Source documents that support the cost basis
- Support for the determination of character of the gain (e.g., ordinary income vs. capital gain)
Significant losses transactions
These are among the most common subjects of IRS reviews. The agency wants to confirm a loss is valid to offset other income. Of particular interest are sole proprietor business losses reported on Schedule C.
To help substantiate losses, taxpayers should retain:
- Invoices
- Receipts
- Bank statements
- Proof of payment
- Documentation that demonstrates the business purpose of each expense
The IRS may recharacterize ongoing sustained losses as a nondeductible “hobby loss” if there is insufficient proof of intent to generate a profit. Taxpayers need to take active steps to substantiate a profit motive and show the business is operating in a business-like manner.
The following actions can help legitimize a business and illustrate a commitment to profitability:
- Establish a formal business plan
- Maintain a separate business bank account
- Secure necessary licenses and permits
- Engage with industry professionals
- Limit any personal or recreational use of resources
Taxpayers need to maintain their basis schedules on a contemporaneous annual basis to make sure the losses can be deducted.
Charitable donations
The IRS scrutinizes cash and noncash donations. Taxpayers should ensure they receive contemporaneous written acknowledgment letters at the time of a donation, as this documentation is crucial for substantiating their deductions.
- For cash donations, retain proof of payment
- For noncash donations, taxpayers should familiarize themselves with the rules regarding when an appraisal is required to support the value of the contribution
Adhering to these guidelines will support compliance and strengthen the legitimacy of deductions claimed.
Utilization of a previously generated net operating loss
Even if the statute for a net operating loss (NOL) from a prior year is closed, it can still be scrutinized in the current year to verify its validity. Careful recordkeeping is essential to support compliance and defend against potential IRS inquiries. Diligently retain all relevant documentation related to the NOL, including:
- Schedules K-1
- Business records
- Records of asset dispositions
- Documentation of any disasters that may have contributed to the loss
Passive and nonpassive activities
The IRS focuses on differentiating between the two. By maintaining thorough documentation, taxpayers can better demonstrate their active involvement and provide a strong defense against potential IRS scrutiny.
Taxpayers should diligently maintain comprehensive time logs and calendars to document the hours spent on each activity, as this is essential for substantiating material participation. Time logs should be detailed, clearly outlining the hours worked along with descriptions of tasks and duties performed.
Personal use of corporate aircrafts
Aircraft taxation is complex, and the need for accurate recordkeeping is essential—especially now that this is a formal IRS campaign. Taxpayers that own or use noncommercial aircraft need to evaluate their preparedness for an IRS examination by reviewing their policies, procedures, documentation, flight logs, tax positions and other implications.
The agency typically assumes personal use unless the company can substantiate business use. Therefore, it is essential that a business has readily available records and documentation related to the following:
- Purchase, operation and, if applicable, sale of the aircraft
- Detailed flight records, including:
- Number of passengers on each flight
- Purpose of each passenger
- Expenses related to operating the aircraft
- Lease or charter agreements
- Aircraft management agreements