It all depends on your family situation. If all involved are reasonable people then things can go well. In my case it turned out that reasonable had nothing to do with it. When my Father passed it took over a week for me to find out about it from a distant relative because my two brothers didn't want me to know. By the time I got involved my brothers and their wives had gone through my dads house like gypsies in the palice. Watches, jewelry, household goods you name it, all gone. They had even located the original will and torn pages out of it that concerned my part of the inheritance. The whole thing turned out to be two full years of misery for everyone. Fortunately for me they decided to share a lawyer on the cheap who hadn't practiced in over 20 years and I went all in with best money could buy. My take on it is that what is owed to the estate is owed and should be payed back. On the other hand if it's going to cause contraversy don't sweat the small stuff, focus on the big picture and know that a lot of things that go to litigation can sometimes end up costing more than they're worth.
Edit: Oh by the way my lawyer was finally able to locate the storage unit where my brothers were hiding my dad's stuff and we retrieved all but one watch. A week later this arrived at my door sent by my youngest brother and we called it even.
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When my grandfather died in 1975, a neighbor woman had been shopping and running errands for him.It might not be seen as fair by an accountant but I've twice taken the high road in family money matters and feel it it is the best way to go. Warring with family is expensive mentally and can be financially.
In closing my mother in law's estate going on for a year now the attorney did bring up one point of inequity discovered between my wife and her brother. It was much better for a practiced family law professional to propose a solution than my wife. The attorney's knowledge with experience made it hard for a sister in law trying to manipulate her brother.