Essential Questions You Have to Ask Your Aging Parents
October 1, 2021

Think the birds and bees is the most awkward chat you'll ever have with Mom and Dad? Think again. Adulthood brings other uncomfortable conversations: wills, long-term care, and end-of-life issues. Here's how to these handle delicate subjects with care.


The Big Question: Do You Have a Will?

A will determines the future of not only money and property but also pets and even token mementos. When someone dies without a will, her estate is divided in probate court, where a judge decides who gets the assets. This can cost thousands of dollars and take months. Even if the deceased told a loved one her wishes before she died, a verbal statement won't hold up in court. The judge will base his ruling on laws and legal precedents of the state."


How to Bring It Up

"I don't want to upset you, but if something happened to you, I would want to know that your wishes were being honored. Do you have a will?"


While You're at It, Ask…

  • Have you consulted a reliable financial planner who can help anticipate your needs as you age?
  • Will you give me or another trusted person power of attorney over your financial affairs in case there's a time you can't handle them yourself?
  • Do you have an authorized user on your bank and investment accounts?
  • Do you need help handling some of your financial ponsibilities, like double-checking your credit-card statements and reviewing your bills?
  • Are you willing to have a joint checking account with me so I can help you pay bills if necessary?


On Their Living Situation…

The Big Question: Have You Thought About Long-Term-Care Insurance?

Most long-term assisted-living or nursing-home expenses are not covered by Medicare.. And long-term care, which includes anything from extended home assistance to a nursing home, is very costly.


How to Bring It Up

"I read about how much assisted living can cost, and I was stunned. I would want you to have the best care if it ever came to that. Have you looked into insurance?"

While You're at It, Ask…

  • Do you want to live in your house for as long as possible? Are there things we need to do to your house so it's safe and comfortable for you as you age? Can we make some of those changes now?
  • Are you willing to move into a smaller place that's easier to manage, like a condo? When?
  • Have either of you thought about whether you would want to stay in the house if you were alone?
  • Would you be willing to hire someone to help you at home if you can't do it on your own anymore?
  • Would you consider moving in with me or one of my siblings if we all agree that you need help with your personal care or aren't safe at home alone anymore? How do you feel about moving into an assisted-living facility?
  • Can I help you scout out quality assisted-living facilities and nursing homes now, so we know what's available and what you would prefer in case you need one in the future?


On Their Health…

The Big Question: Do You Have Advance Health-Care Directives?

Advance health-care directives can include a living will (which gives written instructions on the degree of life-sustaining measures that should be taken), a health proxy in Massachusetts by Statute (which appoints another party to make health-related decisions in the event that a person is unable to do so), and a HIPPA release (a document that allows another person access to someone's medical records, which is useful for insurance claims). It's difficult to make decisions in a crisis, and memories about conversations differ.


How to Bring It Up

"If you were ever on life support, I would be really torn up and not in the best frame of mind to make a decision. I know we talked about how you feel, but I think it would give both of us some relief if you put it in writing."


While You're at It, Ask…

  • Will you consider giving your doctor permission to talk to us in case we have questions about your medical treatment?
  • Can one of us accompany you to some doctor's appointments? We recognize your right to privacy, but maybe we can help keep track of everything your doctor says at your visit.
  • How do you feel about being kept alive with ventilators, feeding tubes, or other interventions? And under what circumstances would you want that? Do we all understand what these terms mean?
  • If you have advance-care planning documents, where do you keep them? Have you shared them with any family members, doctors, or clergy.
Contact us in Belmont, Massachusetts, at (617) 489-5919 for comprehensive estate planning from attorneys with experience.
By Dale Tamburro • September 17, 2026
7 Steps Before Meeting With an Estate Planning Attorney Takeaways You do not need to have every estate planning decision finalized before meeting with an attorney. A basic inventory of your assets can help you avoid overlooking important property or accounts. Identifying potential beneficiaries and an executor can make the conversation with your attorney more productive. Blended families, minor children, beneficiaries with disabilities, and other family circumstances may require special planning. Existing wills, trusts, and beneficiary designations should be reviewed together as part of your overall estate plan. Making a will is easier when you prepare before meeting with an estate planning attorney. You do not need to have every decision finalized, but gathering information about your assets, loved ones, and wishes can help your attorney understand your situation and identify issues that may need special attention. Your attorney can help evaluate your options and decide what type of estate plan is right for you. Here are seven steps to take before a meeting with an estate planning attorney. 1. Make a Basic List of Assets Your assets are everything you own, including: Your home or other real estate Bank and investment accounts Vehicles Valuable personal property, such as jewelry, artwork, collectibles, or family heirlooms Business interests Life insurance Making a list of everything you own can help you in several ways. First, it helps you take stock of your assets and avoid forgetting something you wish to include in your estate plan. Writing down your assets can also help you start to think about the people you may want to inherit your property. 2. Gather Important Documents If possible, gather copies of documents that may help your attorney understand your finances, family situation, and existing estate plan. You may want to bring: Any existing wills, trusts, or amendments Powers of attorney and health care documents Deeds or other records for real estate Recent bank, investment, and retirement account statements Life insurance policies Beneficiary designation forms Business ownership records Prenuptial or postnuptial agreements Divorce decrees or property settlement agreements Information about jointly owned property or accounts Documents relating to a beneficiary with a disability or special needs If you cannot find a document, make a note of the account or property, the institution that holds it, and its approximate value. This information may still help your attorney while you look for supporting records. Bring copies when possible and keep your original documents. Your attorney can tell you which documents are most important for your situation and whether anything else is needed. 3. Identify Your Beneficiaries Before your appointment, make a list of the people and organizations you may want to benefit from your estate plan. This could include: Your spouse or partner Children, stepchildren, grandchildren, or other family members Friends or other people who are important to you Charities, religious organizations, or other nonprofits For each person or organization, think about what you would like them to receive. You might want to leave someone a specific item, such as a piece of jewelry, a vehicle, or a family heirloom. You might also want to leave a specific dollar amount, a percentage of your estate, or the remainer of your property after other gifts have been distributed. Also consider backup plans. For example, who should inherit if a beneficiary dies before you? If you have minor children, should their inheritance be held in a trust until they reach a certain age? If a beneficiary receives government benefits or has difficulty managing money, should their inheritance be handled differently? You do not need to have all these decisions finalized before meeting with your attorney. Jotting down your initial thoughts can help your attorney explain your options and identify issues you may not have considered. 4. Think About Who Should Serve as Your Fiduciary Fiduciaries are the people you name in documents like health care proxies (proxy), power of attorneys (attorney-in-fact or agent), wills (personal representative or executor) and trusts (trustees). This individual should be someone you trust to act responsibly and ethically. You may also want to consider their ability to manage the administrative demands of the role. You also should have a backup in mind in case your first choice won’t or can’t act in the given role. 5. Note Family Circumstances That May Affect Your Plan Before meeting with an estate planning attorney, take note of any family circumstances that could affect your estate plan or how you want to distribute your assets. Important details may include: You have children from a previous relationship or a blended family You are unmarried or have a long-term partner You have minor children and need to consider who you would want to care for them if you and the other parent could no longer do so You have a child or other beneficiary with a disability A beneficiary receives needs-based government benefits You provide financial support for a parent, grandchild, or another dependent You want to leave different amounts or types of property to different family members You are considering leaving someone out of your will You have concerns about a beneficiary’s ability to manage money You own property with someone else or have a family business These circumstances do not necessarily mean that your estate plan will be complicated. However, they may affect whether a simple will is appropriate or whether you should consider additional planning, such as a trust. For example, a beneficiary with a disability who receives needs-based benefits may need an inheritance handled through a special needs trust rather than receiving it directly. 6. Gather Existing Beneficiary Designations Next, review your existing beneficiary designations. These may appear on retirement accounts, life insurance policies, and payable-on-death or transfer-on-death accounts, which often pass directly to the named beneficiaries and may not be controlled by your will. The rules can vary depending on the account and the way it is owned, so bring copies of your designations to your attorney. Through the estate planning process, some people find they want to change or revise their designations on accounts and policies. Others sometimes realize they still need to add a beneficiary. 7. Bring Questions for the Attorney Finally, think about any questions you may have for the attorney. You might want to ask about planning for pets, digital assets , best practices for document storage, or what other estate planning documents you may need. Thinking of questions in advance can help you make the most of your first appointment.
By Dale Tamburro • September 17, 2026
 Takeaways Do not rush into selling, renting, or moving into an inherited house before confirming ownership and financial obligations. Your main options may include moving in, selling the property, renting it, or buying out other heirs. Inherited real estate generally receives a new tax basis tied to its value when the owner died, but the tax result depends on the property and the transaction. Disagreements among siblings, Medicaid concerns, trusts, mortgages, and out-of-state property may require advice from an attorney or tax professional. Inheriting a house can create both financial opportunities and difficult decisions. The property may be a valuable asset, a family home filled with memories, or an expensive responsibility that you do not want to manage. You may be wondering whether to move in, sell the property, rent it out, or share it with other heirs. Before choosing an option, confirm who owns the property, understand the costs, and consider the legal and tax consequences. Start With These Immediate Steps You do not have to decide the property’s long-term future immediately. But you should take steps to protect the house and understand the situation. Confirm Who Owns the Property Review the will, trust, deed, probate filings, and other estate documents. The person named in a will may not automatically have complete authority to sell or transfer the house while the estate is being administered. Ownership may also be affected by joint ownership, a transfer-on-death deed, an irrevocable or revocable turst or state-specific probate rules. Before signing a listing agreement or transferring the property, confirm that the correct person or people have authority to act. Protect and Maintain the House Make sure the property is secure and continues to have appropriate insurance coverage . Insurance agents must be notified of the death of the owner/occupant. If no one is occupying the property, the insurance cost will change. If the insurance agency is not notified you may be denied a later claim. Depending on the circumstances, you may also need to: maintain utilities pay property taxes address urgent repairs protect the house from weather or other damage If the property has a mortgage, home equity loan, or reverse mortgage, contact the loan servicer. Do not assume that you can simply ignore the loan or transfer it to an heir. The estate documents, loan terms, and applicable law may affect what happens next. Gather the Financial Information Collect documents showing: The current mortgage balance and monthly payment Property taxes and insurance costs Homeowners association fees Utility and maintenance expenses Liens or other claims against the property Recent appraisals or assessments Records of major improvements Rental income, if the property was previously rented This information can help you compare the cost of keeping the property with the likely proceeds from selling it. Should You Move Into the Inherited House? Moving into the house may make sense if it is in a location you want, meets your needs, and can be maintained within your budget. Before moving in, consider: Whether the house needs repairs or accessibility modifications The cost of property taxes, insurance, utilities, and maintenance Whether there is a mortgage or other debt Whether you can afford the house over the long term Whether other heirs also have ownership rights Whether moving would affect your work, health care, or family responsibilities If you inherit the property with siblings or other people, moving in does not necessarily give you the right to make all decisions about the house. Co-owners may need to agree about repairs, expenses, use of the property, and whether anyone should pay rent. Put agreements among co-owners in writing. A written agreement can address who may live in the home, which expenses each person will pay, how repairs will be approved, and what happens if someone later wants to sell. Should You Sell the Inherited Property? Selling may be the most practical option when multiple heirs want to divide the asset, the property is expensive to maintain, or no one wants to live nearby. Before listing the house, consider: Its current market value Needed repairs and preparation costs Real estate commissions and closing costs Existing mortgages, liens, and unpaid taxes The timing of the probate or trust administration Whether all owners must sign the sale documents The possible income tax consequences A sale can provide a clean separation among heirs. However, disagreements about the listing price, repairs, timing, or distribution of proceeds can delay the process. An appraisal may help establish a fair value before one heir buys out the others or the property is listed. Should You Rent the Inherited House? Renting the property may create income and allow the family to keep the home as an investment. It also creates ongoing responsibilities. Consider the cost of: Property management Repairs and routine maintenance Insurance and property taxes Vacancies and unpaid rent Tenant screening and legal compliance Accounting and income tax reporting Disagreements among co-owners If several people inherit the house, decide in advance who will manage it, how rental income will be divided, and how large expenses will be approved. A property that produces rental income can still be a poor investment if the owners cannot agree or the maintenance costs are too high. What If You Inherited the House With Siblings? When siblings inherit a house together, the property cannot be physically divided as easily as cash or investments. The heirs generally need to agree on one of several arrangements. Options for Handling a House Inherited With Siblings Option May Work Best When Main Issue One heir buys out the others One person wants to keep the home Agreeing on a fair value and payment terms Sell the property The heirs want to separate their interests Repairs, sale costs, timing, and division of proceeds Rent the property Everyone wants ongoing income Management, expenses, vacancies, and future disagreements Mediate the dispute The heirs disagree but want to avoid court Everyone must participate in good faith If the heirs cannot reach an agreement, a court proceeding may be available in some states to resolve co-ownership disputes. The rules and procedures vary, so consult an attorney in the state where the property is located before taking legal action. What Are the Tax Consequences? The tax consequences depend on a variety of factors, including: the property’s value how it is used when it is sold the applicable state law For federal income tax purposes, the basis of inherited property is generally its fair market value on the date the owner died. If you sell the property for more than your adjusted basis, you may have a taxable gain. If you sell it for less, you may have a loss, although the tax treatment can depend on how the property was used. The Internal Revenue Service (IRS) explains how basis applies to inherited property . The IRS also provides information for executors and administrators about selling or disposing of inherited property in Publication 559 . Keep documents showing the property’s value at the owner’s death. Also hold on to appraisal reports, improvements, selling expenses, and other costs. Ask a tax professional how to determine and document the basis before filing a return or completing a sale. When Should You Get Legal Advice? Consider consulting an attorney before making a major decision if: The property is still going through probate A trust owns the property Multiple heirs disagree about what to do One heir wants to live in the house The property has a mortgage or reverse mortgage The home is located in another state A beneficiary receives Medicaid or other needs-based benefits The property may be subject to estate recovery Someone wants to give or transfer their share to another person There are questions about undue influence, debts, or the validity of the will An elder law or estate planning attorney can help coordinate the property decision with Medicaid planning, trusts, incapacity planning, and the rest of the estate. Learn more about using estate planning to prepare for Medicaid and the difference between elder law and estate planning . Questions to Ask Before Deciding Before moving in, selling, renting, or agreeing to share the property, ask: Who legally owns the property right now? What debts, taxes, insurance, and repairs must be paid? What is the property worth in its current condition? What does each heir want to happen? Can the heirs afford to keep the property? What will happen if one heir changes their mind later? What are the legal and tax consequences of each option? Answering these questions can help the family make a decision based on financial facts rather than pressure or emotion. Make a Decision That Fits Your Circumstances There is no single best choice for every inherited house. Moving in may preserve a family home but create ongoing costs. Selling may provide clarity but require difficult conversations. Renting may produce income but comes with landlord responsibilities. Keeping the property with siblings may work, but only if the owners have a clear agreement. Take time to understand the property and document its value. Communicate with the other heirs and obtain professional advice when the situation is complicated. A thoughtful decision can help protect the value of the inheritance and reduce future conflict.