Raymond Hall, EA

Many families hold an annual meeting about their finances. Whatever else it covers, one part of it can be both short and useful: an annual tax and estate document check-in. Thirty to sixty minutes, once a year, with the right people and a fixed list. The goal is not to decide investment or estate strategy. It is to confirm that the documents are current, that each person knows what they will receive and file, and that anything that changed during the year reaches the preparer and counsel before year end. This post gives an agenda for an annual family tax and estate document check-in, what to bring, and how to record the outcome. It is not a guide to family governance, and it is not tax or legal advice for any person. It is a structure for a meeting that produces a list of actions with names and dates. When and who Hold it in October or early November. Third quarter estimates are paid, extended returns are filed (the extended deadline for 2025 individual returns was October 15, 202...

Parents often put off talking with adult children about family assets because the conversation feels like it is about money, fairness, and expectations. Those are family matters, and no tax preparer should referee them. But there is a narrower conversation that is easier to have and harder to skip: what tax and estate documents exist, where they are, who the children will need to call, and what the children are already responsible for on their own returns. Children who know those facts are less likely to miss a filing, lose a basis record, or learn about a trust from an IRS notice. This post covers what adult children should know about the family's tax and estate documents, and what the parents can share without discussing amounts or plans they want to keep private. It is not family counseling, it does not recommend how much to share, and it is not estate planning or legal advice. Separate the facts from the numbers Most families can share the existence and location of documen...

Estate documents are signed at one moment in a family's life and then read at another. In between, people move, marry, divorce, have children, buy property in other states, and form entities. The documents often stay the same. For tax purposes, the most common gap is residency: a plan drafted for one state's rules now governs a household that lives somewhere else, owns real estate in a third state, and files nonresident returns in a fourth. This post covers the tax facts that tend to drift away from an estate plan, and the records that let your attorney see the drift. It is not estate planning advice and it does not tell you what your documents should say. Drafting belongs to counsel. The goal here is to give counsel and your preparer the current facts. Why residency matters at death For 2026, the federal estate and gift basic exclusion amount is $15,000,000 per person, and it is indexed for inflation in later years. Many households will never owe federal estate tax. State...

Households with significant assets usually end up with one of three arrangements for managing their finances: a single-family office (SFO) that the family owns and staffs, a multi-family office (MFO) that serves many families for a fee, or a set of outside advisors coordinated by the family or by one trusted person. The choice is about service, control, and cost, and those are not tax questions. But each arrangement has different tax consequences: who the employer is, which entity pays the fees, whether those fees are deductible, and what returns and payroll filings follow. This post covers the tax and entity consequences of each arrangement for 2026. It does not recommend one, it does not evaluate any provider, and it is not investment or legal advice. It is what your preparer will need to know once the family has chosen. The fee deductibility problem For individuals, investment management and advisory fees are miscellaneous itemized deductions under IRC Section 212. The 2017 law...

Some advisors describe family wealth in four parts: financial capital (money and assets), human capital (the family's skills and earning power), intellectual capital (knowledge and experience), and social capital (relationships and giving). The framework is about values, and values are not a tax subject. But each of the four leaves a tax and document trail, and families who use the framework often forget that every one of them shows up somewhere in a return, a gift tax filing, or a payroll record. This post maps each of the four kinds of family capital to the tax rules and records that touch it. It is not a values framework, a governance plan, or investment advice. It is a way to make sure the records match whatever the family decides to do. Financial capital: the obvious one Financial capital produces the familiar tax documents: 1099s, K-1s, closing statements, and trust returns. The records that most often go missing are not income records but basis and ownership records: ...

Investments in space, defense technology, and other frontier companies tend to arrive through unusual paths: a friend's seed round, a special purpose vehicle (SPV) organized by a syndicate lead, a convertible note, or shares received for advising a startup. Whether to invest is not a tax question. But each of those paths produces a different tax record, and the records are often thin. Years later, the household needs to prove basis, holding period, qualified small business stock status, and value for gifts, and the company may have moved on, merged, or closed. This post covers the tax and document questions to ask at the time of an early-stage investment in a frontier company, and the records to keep afterward. It is not investment advice, it does not evaluate any company or technology, and it is not buyer diligence. It is a list of what your preparer and counsel will need from you later. First question: what exactly did you buy? The instrument decides the tax treatment. Write...