Another poster is asking about acting as an executor for a parent's will, which is prompting me to ask about other people's experiences of being executors and handling monies owed to the estate.
Long story short, DH is one of his Dad's executors, along with another sibling. FIL has lent money to all his children at one time or another, mostly to help pay for university as it's v. expensive here in the USA.
He keeps meticulous records and as far as DH knows, all have repaid him completely except for one sibling - who's borrowed even more. This sibling has previously said that they'll be paying Dad back forever" so DH guesses we're talking many thousands. 
The estate will be split equally between the siblings and to do it fairly, DH and the other executor will have to take these debts out of her portion, which could be v. awkward.
Has anyone else had to do this and did it cause family ructions? Poor DH hates rows, but if this sibling really does owe the estate thousands, how else can the executors divide it fairly?
I'm only asking because FIL is nearly 80 and DH will probably have to address this in the next few years. 