It bothers me that my large collection of legally bought, drm-free, works (ebooks and digital games, mostly) will basically transform into illegal warez for my heirs, as I understand the law. They can still legally watch my DVDs, read my printed books, but my collection of tabletop RPG PDFs, GOG games, etc, they may as well have downloaded from some shady torrent site? That does not feel right.

Especially not since many things I bought, like from Humble Bundles, have not been available drm-free since, and may never be, so all legal drm-free copies will expire as the generation that bought them passes away?