My experience in the past when family members passed away was that I changed the account to my name and Amazon moved the stuff from the changed account to my main account. They could not move stuff that was no longer available for sale at Amazon. This has been some years now, so don't know if they do the same thing today. I doubt a will will have any traction in this area, but you could certainly try.
There is no guarantee that things will be in the cloud at any time, so best to have de-drm'd copies on at least 2 hard drives and update libraries for family members. Put ID on your external hard drive and indicate who should get that.
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