Am I going to run into problems going from 4.9-stable
Nope-- this shouldn't be any problem.
If I can sneak in a second question. With this openssl fix, couldn't I just apply the patch, cd /usr/src/crypto/openssl && make install ? Instead of the recommended buildworld fiasco?
Certainly you could do so, but the security fix would only apply to programs which dynamicly link the OpenSSL library. In order to fix any staticly linked binaries, you'd need to recompile them as well, which is why the buildworld procedure is generally recommended.
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