High-net-worth tax planning is rarely about a single deduction. It is about the order in which income is recognised, the entities that recognise it, and the structures that hold the assets producing it.
1. Entity architecture. The difference between an S corporation, a partnership and a disregarded entity is not cosmetic — it determines self-employment exposure, basis, and how a future sale is characterised. We model the structure against your five-year plan, not last year's return.
2. Timing and character. Accelerating deductions and deferring recognition only helps when the marginal rate in each year is modelled. Character — ordinary versus capital — is frequently worth more than timing.
3. Charitable and insurance vehicles. Properly designed, these convert obligated dollars into controlled dollars while satisfying genuine planning goals.
4. §1031 exchanges. For real estate operators, a disciplined exchange programme compounds. The failure mode is almost always administrative, not legal.
5. Documentation. A strategy you cannot defend is a strategy you do not have. Every position we take is papered at the time it is taken.
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