We didn't have to do this with my mom, as everything she owned was, of course, willed to him, and all her stuff was there in the house. HE had to decide what he kept, or at least where he'd store it, but he kept us out of that, quite deliberately, because he felt we all had enough to deal with. She's still there, though, in effect, because so much of the material was both of theirs, and she didn't die that long ago either (2000).
At least he lived to see my book published, and to his surprise and mine to actually enjoy reading it (he had mostly stopped reading SF/F years ago, and this wasn't the sort of thing he'd normally like anyway). He even made some very insightful comments on it -- so far he's the only person to have recognized that Jason Wood's narrative style owes a great deal to Archie Goodwin (from Rex Stout's Nero Wolfe novels).
As was characteristic of him, he had arranged most things before he died. And as is characteristic of our family, we've got no real conflicts to deal with here. It's just me and my brother, and neither of us is the grasping sort, so the settling is quiet. Sad, but by now also something to look forward to. My retirement and that of my wife will be, well, not settled, but certainly well started on its way, and the large chunk of liquid funds will allow us to fix up the house we bought to as near-perfect as it can be (eliminate a sunken swampy part of the front yard, build a real workshop/garage, etc.). I think Dad would like the fact that by the time we're done, we'll have a place to live for 10, 20, maybe many more years, and it will be a good place.