Timeshares: Expensive, Hard to Sell, and Even Harder to Value

One of the most troublesome assets we see during estate administration is a timeshare. While it may have been a fun vacation option years ago, a timeshare can become a major headache after death. These properties often trigger probate in another state, are difficult or sometimes nearly impossible to sell, and continue to generate maintenance fees whether anyone uses them or not. In some cases, family members don’t want the timeshare and have no interest in taking on its ongoing costs.

Timeshares are also notoriously hard to value for estate tax purposes, which adds even more complexity to the process. For all of these reasons, if you’re no longer using your timeshare, it’s almost always better to dispose of it while you’re alive. Otherwise, your family may find themselves burdened with ongoing expenses or forced to navigate an out-of-state probate just to get rid of an obligation they never wanted.

Small or Inactive Closely Held Business Interests

Another type of “annoying asset” is an interest in a closely held business that is not well-run, not profitable, or no longer active.

A common example:
Someone’s friend starts a business and invites them to invest—“just buy a couple of shares.” Years later, that business may be:

• Disorganized

• Poorly governed

• Difficult to value

• Impossible to sell

• Worth very little

• Refusing to buy back shares

At death, these minor business interests create a valuation headache on estate tax returns and a logistical headache for the family.

If you own a small stake in a struggling or inactive business and no longer want it, it’s much easier to dispose of it now than to saddle your family with the administrative mess later.

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Why These Assets Become More Difficult After Death

During your lifetime, handling your own assets is relatively simple. You can sign documents immediately, negotiate directly with banks or businesses, transfer ownership on the spot, provide missing information, and make quick decisions about what to keep or sell.

After death, however, everything slows down and becomes highly regulated. Your loved ones must navigate probate court procedures, work within strict legal authority limits, deal with out-of-state asset rules, obtain appraisals, complete tax filings, and wait on third parties such as banks or financial institutions—often for months.

That’s why these “annoying assets” are almost always far easier to manage, sell, or clean up while you’re still alive rather than leaving the burden to your family later.

Estate Planning Is About Making Life Easier for Your Family

A strong estate plan isn’t just about signing a will or a trust—it’s also about organizing your assets in a way that genuinely helps your family. Thoughtful planning reduces stress for loved ones, minimizes the cost of estate administration, avoids unnecessary probate, prevents unexpected taxes or fees, and keeps your affairs streamlined and manageable.

If you own assets that are cumbersome, complicated, or hard to value, the best time to address them is now, not after your family is left to sort through a difficult estate.

Frequently Asked Questions

What are the most problematic assets to leave behind when you die?

Timeshares, small interests in closely held businesses, and having too many scattered bank or retirement accounts are some of the most difficult assets for families to deal with after death. These assets often require extra paperwork, additional probate proceedings, specialized valuations, or lengthy communication with institutions — all of which slow down estate administration.

Should I get rid of problematic assets before updating my estate plan?

Yes. If you own assets that are costly, cumbersome, or difficult to transfer, it’s almost always easier to dispose of them during your lifetime. Cleaning up problematic assets now reduces future probate complications, minimizes stress for your loved ones, and helps ensure your estate plan functions smoothly when it’s needed.

Can consolidating accounts really make estate administration easier?

Absolutely. Consolidating small or inactive bank accounts, old retirement plans, or brokerage accounts significantly reduces administration time and costs. Instead of your family having to contact 10 or 20 different institutions, they can work with just a few — making probate or trust administration faster, smoother, and less expensive.

Author

Claire creates wills and trusts which provide security and peace of mind. She compassionately listens to her clients’ dreams, goals, and fears and then fashions plans that best meet their needs. It is important to Claire that her clients understand different options and make decisions that are right for them. She loves to educate clients by drawing out complicated concepts.

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