I have managed to get OpenSSL 1.1.0h to compile in Scratchbox. Current source tree is at https://github.com/jonwil/openssl/

The openssl test cases are failing on Scratchbox armel (doesn't surprise me given how "unique" scratchbox is in the way it runs the arm binaries and stuff) so I have turned them off in the packaging.
All the tests pass on my N900 so I am going to continue and test the actual packages on my N900 and see what happens.

Once I get OpenSSL working, I will then move onto getting TLS 1.2 support into QT and then getting Fahrplan fixed.