AP> As support for platforms "narrower" than 32-bit is discontinued...
Do I face the prospect of not being able to update at all (past some
0.9.9)?!

Once again, platforms *narrower* than 32-bits are discontinued, in other words 16-bit one[s]. Is your platform 16-bit? I find it hard to believe:-)

As the more code in the OpenSSL gets updated - the more I'll disable in
./configure? Quite sad...

Life is not fair, never was, never will be:-)

AP> How wide-spread the target platform?
It is QNX4. Not as usual as windoze, but still very popular for
robotics...

As far as I understand there is gcc for QNX, so why not use it as "more feature-rich compiler"?

AP> Is SHA512 really required in the context and/or does it really
AP> worth it?
To ensure the interoperability with modern clients on other platforms
(SSH.com, OpenSSH) - yes.

Is there evidence that there will be applications emerging that will refuse to negotiate anything else but SHA-512? I find it hard to believe. I reckon that disabling SHA-512 does not impose risk of reduced interoperability in the time-frame of release-span of any particular platform/compiler. Meanwhile ask your vendor to implement long long support:-) A.
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