My family is nuts on one side and normal on the other. On my Dad's side (nuts) when my grandmother died all hail broke loose. My Uncle was the executor of the will and a lawyer. Any attempt at questioning some of the expenses, appraisals, etc were met with a reminder that he would hire an attorney and spend every ounce of the estate in legal bills leaving everyone with nothing.
My Aunt who always tried to argue with him had spent my grandmother's final months "visiting". I'm sure someone else has experienced this as well. On each "visit" things were discussed such as that antique ships wheel that my Aunt just loved, or jewelry that she just loved. Many things disappeared before my grandmother even died.
What was left turned into a free for all that was refereed by my Uncle (married to the above mentioned Aunt). At one point he actually got a whistle. 3 siblings arguing over this stuff was not a sight for the weak. It was amazing how quickly it could go from a civilized discussion to 5 year-olds arguing over something that happened in the 60's.
The other side of my family was much simpler. My Aunt was the executor of my maternal grandmothers estate. The only asset was the house and my Aunt wanted to buy it. It was the last childhood home they had that hadn't been blown up, but that's another story. She had it appraised 3 times by separate appraisers and we all agreed that the fair value was an average of the three. It was incredibly smooth and no ones feelings got hurt.
In my experience there is no such thing as a simple will and you can never be too specific. After going through a bad estate liquidation I completely understand why some people just leave everything to charity.