Raymond Hall, EA

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...

A household with a preparer, an estate attorney, a corporate attorney, an investment advisor, and an insurance agent has five professionals who each see part of the picture. Most tax problems that reach a notice or an amended return were not caused by anyone's mistake in their own area. They came from a decision made in one area that nobody told the others about: a trade that created a wash sale across accounts, a trust funded without a new EIN, an entity formed without anyone asking how it would be taxed, a move that the investment advisor learned about after the year's gains were already sourced. This post covers how to coordinate advisors around tax events: which decisions need more than one professional, how information should flow, and what written authorizations let advisors talk to each other and to the IRS. It is not a recommendation to hire anyone and it does not replace any advisor's own engagement terms. It is a framework for making sure the tax result of a dec...

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...

A large position in one stock usually arrives the same way: years of equity compensation, a founder's shares, or an acquisition paid in the buyer's stock. At some point the household decides to reduce it. Whether and how fast is an investment decision. But every way of reducing a position has a tax result, and the tax result depends on records that many households cannot produce on short notice: basis, acquisition dates, the type of grant, and any restrictions on sale. This post covers the tax side of reducing a concentrated stock position in 2026: what records to assemble, how the main approaches are taxed, and which questions belong to your preparer, your investment advisor, and counsel. It is not investment advice and it does not recommend any strategy. It is a framework for walking into that conversation with the facts ready. Start with the lot record Before any decision, build a lot-level record of the position. For each lot: Acquisition date and how it was acquired...

Households with uneven income rarely run short of money over a full year. They run short on particular dates. A K-1 shows income in September with no distribution behind it. A property tax bill and a January estimated payment land in the same month. A sale closes in November and the tax on it is due in April, but the proceeds have already been committed. The fix is not a bigger cash balance. It is a calendar that shows when tax money is needed, and an account that holds it until then. This post covers how to build a tax cash calendar for a household with several income streams, how to size a tax reserve, and what records keep it honest. It is not investment advice and it does not recommend where to hold cash. It is about matching tax obligations to the dates they are actually due. Why a flat cash rule fails A rule like "keep six months of expenses in cash" assumes spending is even across the year. Tax is not. For a household with lumpy income, most of the year's tax ...

Households with several accounts, a few partnership interests, and a trust or two receive a stack of statements every quarter. Most of it goes unread. That is usually fine for investment purposes, because someone else is watching performance. It is not fine for tax. The return depends on a handful of facts buried in that stack: basis, holding periods, K-1 timing, state sourcing, and foreign accounts. When nobody pulls those facts out during the year, they get reconstructed in March under deadline pressure. This post covers how to turn the quarterly stack into a tax reporting view: what to extract, when, and who needs it. It is not a review of investment reporting software and it is not investment advice. It is about the documents your preparer needs and the order they arrive in. What the stack is actually for, from a tax view Investment statements answer "how did we do." A tax view answers different questions: What was sold, when, at what basis, and was the holding per...

Households with complex finances eventually decide which tasks to handle with their own staff and which to hand to outside firms: bookkeeping, bill pay, payroll for household employees, tax preparation, investment reporting, insurance review. The choice is about cost and control, and the family makes it. The tax side is simpler than it looks: some responsibilities transfer with the task and some never do. A family can outsource household payroll and still be the employer liable for the tax. It can hire a bookkeeper and still be the person who signs the return under penalty of perjury. This post covers the tax consequences of keeping functions in-house or outsourcing them: who stays responsible, what records each choice produces, and what the household should require from any provider. It does not recommend in-house staff or any provider, and it is not legal or investment advice. What never transfers Responsibility for the return. The taxpayer signs the return under penalty of pe...