Brotman Law — IRS audit defense attorneys in San Diego

Tax Strategy

Complex Tax Issues Strategy

A strategic overview of how Brotman Law approaches complex tax issues cases.

At Brotman Law, we focus on providing as much as we can for our clients. Our strategy pages give you a detailed look at how we approach each type of tax issue – so you can understand what to expect when you work with us.

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Tax Strategy & Optimization

  • Business Tax Optimization
  • Individual Tax Optimization
  • Residency & Multi-State Tax Issues
  • Exit Planning and Other Corporate Transactions
  • Real Estate and Investment Portfolio Optimization

Tax Defense

  • Criminal Tax Defense
  • IRS Audits
  • California Income Tax (FTB)
  • California Sales, Use, and Excise Tax (CDTFA)
  • California Payroll Tax (EDD)
  • IRS Tax Debt Resolution
  • California Tax Debt Resolution
  • Other State Tax Representation

Employee Retention Tax Credit

  • Employee Retention Tax CreditFilings
  • Employee Retention Tax CreditAudits
  • Employee Retention Tax CreditAppeals
  • Employee Retention Tax CreditLitigation

Other Complex Tax Issues

  • International Tax Controversy and Compliance
  • Multi-State Tax Compliance and Voluntary Disclosures
  • Divorce/Legal Separation Tax Issues
  • Cryptocurrency Tax Issues
  • Cannabis Tax Issues
  • Tax Promoter/Tax Shelter Issues
  • Complex Tax Preparation
  • Other Insights

Tax Evasion Penalties Guide & Tax Fraud Jail Time Sentences Blog

Tax Evasion Penalties Guide & Tax Fraud Jail Time Sentences

Can you serve tax fraud jail time? Learn about tax evasion penalties, possibility of a prison sentence for crimes, fines & other tax return laws & punishment

California State Taxes and Federal Regulations: Conflicts Between Federal and California Law

If your business conducts sales to other states, you need to be aware of how California sales tax rules apply to you — especially if you sell online.

California Use Tax Planning for Aircraft and Marine Vessels

As with most other property, the purchase and use of aircraft within California is subject to sales and use tax, but certain aircraft uses and purchases may be tax-exempt.

How to Apply Payroll Taxes for Multistate Employees

Do you have employees in states outside of California? We can help you fulfill the payroll tax requirements for multistate commerce.

California Sales Tax and Leasing Transactions

Did you know what some leases in California may incur sales tax? We will explain what type of leases may be taxed by the state.

Industry Specific California Tax Issues for Out-of-State Companies

Do you want to do business in California but are not located there? Certain types of out-of-state businesses may be subject to California sales and use tax.

State Income and Payroll Tax Considerations in Multistate Tax Planning

Does your business have employees working in other states? If you do, make sure you are abiding by each state’s payroll tax regulations. Learn more.

Is Labor Taxable in California?

The labor that you are using in your business may be taxable. How do you know? Here some pointers from an experienced tax attorney.

How Does Drop Shipping Affect Multistate Taxation?

Drop shipping may be convenient for your business, but it can quickly turn into a multistate tax nightmare. Find out how to save yourself millions.

Am I Eligible for California’s Voluntary Disclosure Programs?

Do you qualify for the CDFTA Voluntary Compliance Program? If your business has not been paying sales tax, help is on the way.

California Multistate Tax Implications for Amazon Sellers

Does your company sell on Amazon? You still are responsible for California sales tax. Find out how to comply.

9 Frequently Asked Questions About Multistate Taxation [Questions + Answers]

A top tax attorney answers your FAQs about e-commerce and multistate sales tax.

What to Do If You Are an Out of State Business and Audited by California

Facing a California sales tax audit? Do not panic. A top tax attorney offers advice on how to respond to a CDTFA notice.

How to Determine Your Tax Compliance With California Blog

How to Determine Your Tax Compliance With California

If you conduct business across state lines, you may still owe California sales tax. Find out how to comply before it is too late.

What Is the Tax Crime of Omission? Blog

What Is the Tax Crime of Omission?

What is the tax crime of omission, and what steps do I need to take if I have been charged with omission of taxes?

What is the Omnibus Clause? Blog

What is the Omnibus Clause?

How can fraud, corruption, threats, and interference trigger the Omnibus Clause, creating liability and penalties for a taxpayer?

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The Audit Process Step by Step

Here's what happens from the moment you receive an audit notice to resolution:

  1. Notice received — The IRS sends a letter explaining what they're examining and what documentation they need
  2. Power of Attorney filed — We sign Form 2848, which means the IRS talks to us, not you
  3. Document review — We review every document before anything goes to the IRS. We provide exactly what's needed — nothing more
  4. Examination — The IRS reviews your records. For office and field audits, we attend all meetings in your place
  5. Proposed adjustments — If the IRS wants to make changes, they issue a written proposal. We review it line by line
  6. Negotiation or appeal — We challenge anything we disagree with. If we can't resolve it at the exam level, we take it to appeals
  7. Resolution — Case closed. We make sure you understand the outcome and what it means going forward

Why You Need Professional Representation

Here's the reality: anything you say to the IRS can be used against you. Even an innocent statement can be misinterpreted, taken out of context, or used to expand the scope of your audit.

Your CPA probably filed your return. That's great. But filing a return and defending one are two completely different skills. You wouldn't send your dentist to perform heart surgery — the same logic applies.

A qualified tax attorney knows IRS procedures inside and out, understands the legal standards the IRS must meet, and knows exactly how to position your case for the best possible outcome.

Appeals & Next Steps

If you disagree with the audit results, you have the right to appeal. The IRS Office of Appeals is independent from the examination division, and they settle the majority of cases they hear.

We've won over 100 appeals by building cases that are thoroughly documented and legally sound. The key is presenting a clear, well-organized argument that makes it easier for the appeals officer to rule in your favor.

If appeals doesn't resolve it, the next step is Tax Court. We're prepared for that too, but in our experience, most cases settle well before they get to trial.

How to Prevent Future Audits

Once your audit is resolved, the last thing you want is another one. Here's what we recommend to minimize your risk:

  • Keep meticulous records — especially for deductions and business expenses
  • Report all income — even if you didn't receive a 1099
  • File on time, every time
  • Use actual calculated figures rather than round numbers — while not a major audit trigger on its own, it's a best practice that signals accuracy in your records
  • Work with a qualified tax professional who understands your situation
  • Consider a proactive tax strategy engagement to optimize your structure and reduce risk

Want to make sure this doesn't happen again? After resolving your audit, we can help restructure your taxes to minimize future risk. It's the other side of what we do — and it's just as important as the defense. Learn about our tax strategies →

Related Resources

View Our Complex Tax Preparation Services →

Read the Multistate Tax Guide →

Frequently Asked Questions

Complex Tax Issues Strategy FAQs

What qualifies as a "complex" tax issue?

Complex tax issues involve situations where multiple areas of tax law intersect, where the facts don't fit neatly into standard categories, or where the financial stakes require a higher level of analysis. Examples include business restructuring with tax implications, multi-entity ownership structures, cryptocurrency and digital asset taxation, cannabis tax compliance (Section 280E), exit planning and M&A transactions, and cases involving both federal and state controversy simultaneously.

When should I hire a tax attorney instead of a CPA?

A CPA is the right choice for tax preparation, bookkeeping, and straightforward compliance. A tax attorney is essential when you face potential legal exposure — audits, collections, penalties, criminal investigation, or any situation where attorney-client privilege matters. For complex planning (entity restructuring, exit transactions, international issues), the ideal approach is a tax attorney and CPA working together. We regularly collaborate with our clients' CPAs to ensure both compliance accuracy and legal protection.

How does Section 280E affect cannabis businesses?

IRC Section 280E prohibits businesses trafficking in controlled substances from deducting ordinary business expenses — even if the business is legal under state law. This means cannabis businesses often face effective tax rates of 60-80%. The only deduction allowed is cost of goods sold (COGS). Proper structuring of cannabis operations, meticulous COGS documentation, and strategic entity planning can significantly reduce the 280E burden. We represent cannabis businesses in both planning and IRS defense.

What tax issues arise when selling a business?

The structure of a business sale — asset sale vs. stock sale, installment sale vs. lump sum, allocation of purchase price among asset classes — dramatically affects the tax consequences for both buyer and seller. Other considerations include depreciation recapture, state tax apportionment of the gain, potential Qualified Small Business Stock exclusions (Section 1202), and the timing of recognition. We work with business owners well before a sale to structure the transaction for optimal tax results.

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