Some of my siblings are essentially homeless and want some stuff. These are items with more sentimental value than market value. For example, my mom has a chair that crossed the plains in a covered wagon. I don't care who it goes to except that I want it to be respected and passed to future generations, not sitting in a storage unit where an unpaid bill could cause a loss to the family. If one of my siblings doesn't have the capability to protect the asset, I don't want them to have it, as do all of the other siblings, which means there could be some squabbling I guess.

My wife's siblings? Not sure if there are similar items, but all of her siblings are stable, so I doubt there will be issues.

One key is to have those discussions solely with siblings. No spouses (in laws) allowed in the discussions. They are usually the ones that cause problems.