I recently attended a reunion for Satellite Beach High School in Florida, from which my wife and I graduated back in 1985. It was a lovely event that allowed me to reconnect with many old friends. I got to play bad golf with my old teammates from our bad golf team, hang out on the beach and of course reminisce about the old days.

My, how things have changed. Some change is good. We are all grateful that the wardrobes and hairstyles of the mid-’80s disappeared and, my goodness, we are thankful there isn’t any cell phone evidence of some of our displays of stupidity. We Scorpions laughed a lot over the weekend, but we also lamented other changes.

For instance, the list of our departed classmates is longer. We’re also older, and staying up late takes a harsher toll. Several times, we found ourselves comparing medications and complaining about the government like a bunch of elderly curmudgeons. Sadly, almost everyone I talked to told a tale about the trial and tribulations of helping their parents or other older adults manage health issues.

Many of these stories will be familiar to financial planners reading this column.

My friend Billy’s mom was hospitalized for sepsis, a deadly blood infection. As is commonly the case, she had significant cognitive and physical impairments because of the infection and was sent to a rehab center to recover. Billy found he could not get his mom’s household bills paid because nobody had authority to disburse money from her checking account but her.

My friend Chris’s mom passed away in 2017. Though the estate was relatively simple, it took her some time to finish the settlement. The issues came about when the estate was probated. Chris’s “dad” tried to contest the will and claim some assets. The quotations are used here because he left home when Chris was in diapers, and she had had no relationship with him, hadn’t spoken to, heard from or even heard about the man since she was in college over 30 years ago.

Your head is probably going the same place mine did during these conversations. Both these situations would have been preventable with some planning and proper documentation. Billy’s mom could have put her accounts in a trust, executed a power of attorney, or added a joint owner. All of those options have pros and cons, of course, but all could have helped the bills get paid.

Fortunately, Billy’s mom recovered well and was able to get her documents squared away. A couple of years later, she fell ill for an extended period and Billy was able to manage her affairs before her passing.

Chris’s plight may have been prevented if her mom hadn’t relied strictly on a will for the asset transfers. The will turned out to be fine. It said what she wanted it to and was properly executed. In the end, the assets were eventually distributed as her mom wanted, but between court costs, attorney’s fees, the seemingly endless delays and the stress of the confrontation, the toll was significant.

Things would very likely have been different had Chris’s mom created and funded a garden variety living trust. When her father saw the obit, he could still have caused some trouble, but he would have found far less information in the public records, which is apparently what got him going down this path.

Even worse are the stories people tell about caregiving, a subject that even terrific documents don’t really address.

For instance, the documents don’t help people deal with uncooperative seniors. This is a particularly difficult issue when there’s cognitive decline involved. In my own family, as my dad’s dementia got worse, he would not do many things he was supposed to do. For instance, when he passed, we found lots of pills he stashed in weird places instead of swallowing them.

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