It probably never should have been assumed that Jerry Garcia's estate administration would go smoothly, after he passed away in 1995. At first, it did seem that maybe there would not be any major problems.
However, Garcia passed away after being married three times, having four children and having one stepchild.
Even after his third wife threw the first two wives out of his funeral, it did not necessarily mean the estate administration itself would go wrong. No one challenged his will, for example.
The big mistake came when the third wife, Debra Koons, was chosen to administer the estate, as the Wills, Trusts & Estates Prof Blog discussed in "The Wrong Executor Can Make Family Drama Worse, As Jerry Garcia's Heirs Discovered."
The problem for Garcia's estate is that his other heirs objected to many of the decisions that Koons made. They felt she was acting in her own interests and not in the best interests of everyone.
This led to constant family squabbles and made the estate administration more costly and time-consuming than it needed to be.
The problems should have been anticipated.
It would have been wiser to have an independent professional hired to handle the administration of the estate. That might not have been a solution to all of the problems, but it would have taken much of the family drama out of the situation.
Reference: Wills, Trusts & Estates Prof Blog (Oct. 12, 2017) "The Wrong Executor Can Make Family Drama Worse, As Jerry Garcia's Heirs Discovered."