Basic "I'm not too worried about it" level of security: stick it on a webserver using .htaccess to demand a password. Make that password halfway decent.

Better option: export to PDF by either exporting to HTML or latex and then using that system's PDF export. Keep both PDF and original in a folder on Google drive or Dropbox that is shared only with those who need access. (No password needed at all so you won't have someone compromising you with a crap password)

Best option: same thing but store those files in a respected password manager like 1password or keepass. Train your family to use the password manager. Use it as a vault for all sorts of "just in case, they should know" info.

In theory, you could even automate things to work on a deadman's switch. Have a system that pings you via email, SMS, or another communications mechanism weekly. If you don't respond within a few days, it automatically shares the aforementioned files using gdrive, Dropbox, 1password, etc (not email though - email is not secure)

On Fri, Nov 29, 2019, 5:56 AM Marcin Borkowski <mbork@mbork.pl> wrote:

On 2019-11-29, at 08:24, David Masterson <dsmasterson@outlook.com> wrote:

> My use-case is this:
>
> I'd like to use Org to write up *all* the information about my family
> life (so to speak) including medical histories of my family, issues with
> the house, bank accounts, financial information, etc., so that my family
> has all the information to refer to when necessary in a (hopefully)
> well-structured form.  Naturally, this is going to have a fair amount of
> really sensitive information.  By carefully outlining the information, I
> can structure the sensitive information to be in key parts of the
> documents that I can then encrypt using org-crypt.
>
> That part is straightforward.  The tricky part is that my family is not
> "Emacs literate" and, so, I'm thinking the best idea is to export the
> information from Org files to HTML files so that I can then present to
> them as a website.  They are used to browsing the web, so this should be
> more natural to them.  The problem that I'm looking for help with is how
> to deal with the encrypted information?  Any suggestions?

This is a very interesting and important question.  I don't have any
advice, but I would very much like to hear what others have to say.

While this does not answer your question (but is related): who is going
to have the password/passphrase?  Have you considered using a secret
sharing scheme?

Best,

--
Marcin Borkowski
http://mbork.pl