Raymond Hall, EA

Households that hire a full-time employee often choose between someone who lives on the property and someone who comes in each day. The choice is about the family's life and the job. The tax rules treat the two arrangements differently, starting with whether the room and meals count as wages and continuing into overtime, state withholding, and what the household has to document. This post covers the federal tax treatment of lodging and meals provided to household employees, how live-in status affects payroll and the new overtime deduction, and the records to keep. It does not advise on which arrangement to choose, and it is not employment or housing law advice. Wage and hour rules for live-in workers vary by state and belong to an employment attorney. The starting rule: everything of value is wages Unless an exclusion applies, anything a household employer provides to an employee as pay is wages, whether it is cash or not. That includes housing, meals, a car, and phone service....

Entities that once had a clear job tend to outlive it. A management company formed to run a family's finances, an LLC that employed household staff, or a holding company for a business that was sold can keep filing returns, paying state fees, and running payroll accounts long after anyone uses them. When the family decides to close one, merge it into another, or hand the work to an outside firm, the tax side has its own sequence, and skipping a step leaves a filing obligation open. This post covers the federal and state filings involved in closing or consolidating an office or management entity, how the move affects payroll and staff, and the records to keep afterward. It does not advise on whether to close, merge, or keep an entity. That is the family's decision with counsel. This is what the returns and payroll accounts need once the decision is made. Start with the inventory Before anything is closed, list what the entity actually has: Its legal name, EIN, state of for...

Many households give in the last six weeks of the year, often in a hurry, and often by whatever method is closest to hand. For 2026 that habit costs more than it used to. The 2025 tax law changed how charitable deductions work starting this year, and the rules now reward giving that is planned, documented, and matched to the right vehicle. This post covers the 2026 federal rules for charitable deductions, the main giving vehicles and how each is taxed, and the records each one needs. It is not advice on which causes to support, how much to give, or whether to set up a foundation. Those are the family's decisions, and the structure of a foundation or trust belongs to counsel. This is what the return needs once the family has decided. What changed for 2026 Three changes from the 2025 law (Public Law 119-21) apply to gifts made in 2026 and later: A floor for itemizers. Charitable contributions are deductible only to the extent they exceed 0.5% of adjusted gross income. A househ...

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...

A family deciding between candidates for a senior financial role, such as a household chief financial officer, controller, or office lead, will usually score them on competence, fit, and integrity. That evaluation belongs to the family and its advisors. But there is a second scorecard worth running before an offer goes out: a tax and payroll checklist for the role itself. Senior hires often handle the household's tax records, payments, and IRS correspondence. The terms of the job decide who files what, who can sign, and who is responsible if a payroll deposit is missed. This post is a pre-offer tax and payroll checklist for a senior household or office hire, and a short list of tax-related questions a family can ask any candidate about how they handle tax records. It does not evaluate candidates, it is not hiring or employment law advice, and it does not recommend any person or firm. Part one: the role checklist Score each item before the offer. The answers go to your preparer...

When a household or a family office hires its first senior person, such as a chief financial officer, a controller, or a lead administrator, most of the attention goes to the search and the interview. The tax side gets settled in a hurry after the offer is accepted, and that is when the mistakes happen. The person is paid through the wrong entity, treated as a contractor when they are an employee, given a bonus structure nobody has checked against the deferred compensation rules, or set up in a state where the employer has no payroll account. Each of these lands on a return. This post covers the payroll, worker classification, and bookkeeping questions to settle before a senior hire starts. It is not hiring advice, it does not cover how to find or evaluate a candidate, and it is not employment law advice. It is the list your preparer and payroll provider need answered. Question one: who is the employer? Decide which legal entity employs the person. Options include an office LLC or...

Families that create an office or a formal management structure often start with a charter: a document stating the office's purpose, who it serves, who makes decisions, and how it is overseen. Drafting a charter is counsel's and the family's work. But a charter also answers questions every tax preparer needs answered, often in places the preparer never sees. Who is the employer? Which entity pays for what? Who signs returns and authorizes payments? Who can talk to the IRS? If the charter and the tax records disagree, the tax records are what the IRS reads. This post covers what a preparer needs from a family office charter, or from any written description of how a household's finances are run. It is not a drafting guide and it does not tell a family what its charter should say. It lists the tax facts a charter should make clear, so the people preparing returns can work from the same page. Seven questions a preparer needs answered 1. Which entity is the office? Nam...

Households with several entities, accounts, and advisors pay a cost when nobody owns the records. It rarely looks dramatic. It looks like a penalty notice for a missed state filing, an amended return after a late K-1, a lost carryforward, an extension every year because documents arrive in pieces, or a preparer billing extra hours to reconstruct what should have been on file. Each one is small. Together they add up, and some of them cannot be undone. This post puts numbers on what disorganized records cost at tax time, using 2026 penalty and interest rules, and lists the controls that prevent them. It is not a pitch for any system or service. It is a way to see where the money leaks. Penalties with a price tag Late filing and late payment The failure-to-file penalty is 5% of unpaid tax per month, up to 25%. The failure-to-pay penalty is 0.5% per month, also up to 25%. When both apply in the same month, the filing penalty is reduced by the payment penalty. Interest runs on top: th...

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: ...

Most households with more than one state, entity, or income stream do not have a tax problem so much as a record problem. The return gets filed, but nobody can say in October which accounts exist, which entities still file, who holds the signed documents, or whether this year's estimates match this year's income. A one-page annual review fixes that. It takes about two hours once the inputs are gathered, and it makes the next filing season shorter for everyone involved. This post covers what goes on the page, where each answer comes from, and how to score it. It is not a financial plan, an investment review, or a substitute for the preparer's own engagement checklist. It is the household's side of the work: the facts your preparer and counsel need, kept in one place. Why one page A binder gets built once and then goes stale. A single page gets updated because it is short enough to finish. The goal is not completeness in the page itself. The goal is that every line p...

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...