If your concern is security you shouldn't use OpenSSL in the first place.
My pick would be OpenBSD or Gentoo with LibreSSL if it's security wise.
Stable is for servers great because bleeding edge might break once in awhile 
and for decent amount of uptime you want to keep it going without to worry 
about minor updates for packages.
Kind regards,
Y

On September 13, 2016 1:00:24 PM GMT+02:00, Ralph Seichter 
<[email protected]> wrote:
>On 13.09.2016 12:34, Michael Armbruster wrote:
>
>> You all did read my message that Debian can be converted to Arch
>Linux
>> on DigitalOcean, right?
>
>Duly noted (speaking for myself only, of course).
>
>> That would leave you with bleeding edge software as you know it from
>> Gentoo.
>
>I checked https://www.torproject.org/docs/debian.html.en before
>settling
>with Debian Jessie. Using the newest stable Tor was my major concern,
>as
>Jessie comes with Tor 0.2.5.x, if I remember correctly. Getting
>packages
>from deb.torproject.org solves this. Beyond that I am mostly concerned
>with things like OpenSSL, where "cutting edge" is an important issue. I
>haven't used Debian for a long time, so I'll have to do some digging.
>
>-Ralph
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