Resolving missing link to libcrypto openssl on OSX from: http://stackoverflow.com/questions/38670295/brew-refusing-to-link-openssl
brew update
brew install openssl
ln -s /usr/local/opt/openssl/lib/libcrypto.1.0.0.dylib /usr/local/lib/
ln -s /usr/local/opt/openssl/lib/libssl.1.0.0.dylib /usr/local/lib/
working homebrew openssl postgres configure (just stuffing keywords for future searchers)
./configure prefix=/tmp/pg --with-openssl --with-libs=/usr/local/opt/openssl/lib --with-includes=/usr/local/opt/openssl/include