SSL Causing issues with images, fonts, media and plugins

Hi,
I am working on El Capitano 10.11 with WordPress 4.6.1 (localhost) and XAMPP 5.6.28-1. I have two main issues that, for what I could gather online, have to do with the fact that my Mac is using SSL Version => SecureTransport as found out by running php -i | grep "SSL Version". The issues are of two kinds:

1) Error messages on the wp admin such as: Warning: An unexpected error occurred. Something may be wrong with www.ads-software.com or this server’s configuration. If you continue to have problems, please try the support forums. (WordPress could not establish a secure connection to www.ads-software.com. Please contact your server administrator.) in /Applications/XAMPP/xamppfiles/htdocs/wordpress/wp-admin/includes/translation-install.php on line 59 together with issues with uploading plugins (the error message is similar to the one above)
2) Images, fonts and other media do not display as per:

https://www.elegantthemes.com/blog/tips-tricks/ssl-causing-images-not-to-display-heres-how-to-fix-it

I have found a number of references on line, but it is very difficult to navigate through the information and still did not find a cure for it (these are some of the entries found + references in WP forums):

https://stackoverflow.com/questions/32879475/an-unexpected-error-occurred-something-may-be-wrong-with-wordpress-org

https://stackoverflow.com/questions/35238058/error-wp-admin-includes-translation-install-php-on-line-59

https://stackoverflow.com/questions/28261006/how-to-resolve-server-configuration-issue

This is my version of openssl as found out by running the command openssl version -a

OpenSSL 0.9.8zg 14 July 2015
built on: Aug 22 2015
platform: darwin64-x86_64-llvm
options:  bn(64,64) md2(int) rc4(ptr,char) des(idx,cisc,16,int) blowfish(idx) 
compiler: -arch x86_64 -fmessage-length=0 -pipe -Wno-trigraphs -fpascal-strings -fasm-blocks -O3 -D_REENTRANT -DDSO_DLFCN -DHAVE_DLFCN_H -DL_ENDIAN -DMD32_REG_T=int -DOPENSSL_NO_IDEA -DOPENSSL_PIC -DOPENSSL_THREADS -DZLIB -mmacosx-version-min=10.6
OPENSSLDIR: "/System/Library/OpenSSL"

In last instance, I have tried to install MacPort as recommended here:

https://karl.kornel.us/2015/12/el-capitan-need-openssl-install-macports/

I have run sudo port install openssl, but unfortunately I was returned with the following:

Error: Port openssl not found

Can you please help? I am terribly stuck and not able to have my localhost installation working.

This is the output when running brew doctor, not sure if this can give some indication of what my issue is:

Please note that these warnings are just used to help the Homebrew maintainers
with debugging if you file an issue. If everything you use Homebrew for is
working fine: please don't worry and just ignore them. Thanks!

Warning: You have MacPorts or Fink installed:
  /opt/local/bin/port

This can cause trouble. You don't have to uninstall them, but you may want to
temporarily move them out of the way, e.g.

  sudo mv /opt/local ~/macports

Warning: Unbrewed dylibs were found in /usr/local/lib.
If you didn't put them there on purpose they could cause problems when
building Homebrew formulae, and may need to be deleted.

Unexpected dylibs:
  /usr/local/lib/libMonoPosixHelper.dylib
  /usr/local/lib/libqmi_api.dylib
  /usr/local/lib/libSFFileMonitor.32.dylib
  /usr/local/lib/libSFIPC.32.dylib
  /usr/local/lib/libSFIPC.I.dylib
  /usr/local/lib/libSFsqlite3.7.4.dylib
  /usr/local/lib/libSFSyncEngine.I.dylib
  /usr/local/lib/ZTENdis51Service.dylib

Warning: Unbrewed header files were found in /usr/local/include.
If you didn't put them there on purpose they could cause problems when
building Homebrew formulae, and may need to be deleted.

Unexpected header files:
  /usr/local/include/node/android-ifaddrs.h
  /usr/local/include/node/ares.h
  /usr/local/include/node/ares_build.h
  /usr/local/include/node/ares_rules.h
  /usr/local/include/node/ares_version.h
  /usr/local/include/node/libplatform/libplatform.h
  /usr/local/include/node/libplatform/v8-tracing.h
  /usr/local/include/node/nameser.h
  /usr/local/include/node/node.h
  /usr/local/include/node/node_buffer.h
  /usr/local/include/node/node_internals.h
  /usr/local/include/node/node_object_wrap.h
  /usr/local/include/node/node_version.h
  /usr/local/include/node/openssl/aes.h
  /usr/local/include/node/openssl/archs/aix-gcc/opensslconf.h
  /usr/local/include/node/openssl/archs/aix64-gcc/opensslconf.h
  /usr/local/include/node/openssl/archs/BSD-x86/opensslconf.h
  /usr/local/include/node/openssl/archs/BSD-x86_64/opensslconf.h
  /usr/local/include/node/openssl/archs/darwin-i386-cc/opensslconf.h
  /usr/local/include/node/openssl/archs/darwin64-x86_64-cc/opensslconf.h
  /usr/local/include/node/openssl/archs/linux-aarch64/opensslconf.h
  /usr/local/include/node/openssl/archs/linux-armv4/opensslconf.h
  /usr/local/include/node/openssl/archs/linux-elf/opensslconf.h
  /usr/local/include/node/openssl/archs/linux-ppc/opensslconf.h
  /usr/local/include/node/openssl/archs/linux-ppc64/opensslconf.h
  /usr/local/include/node/openssl/archs/linux-x32/opensslconf.h
  /usr/local/include/node/openssl/archs/linux-x86_64/opensslconf.h
  /usr/local/include/node/openssl/archs/linux32-s390x/opensslconf.h
  /usr/local/include/node/openssl/archs/linux64-s390x/opensslconf.h
  /usr/local/include/node/openssl/archs/solaris-x86-gcc/opensslconf.h
  /usr/local/include/node/openssl/archs/solaris64-x86_64-gcc/opensslconf.h
  /usr/local/include/node/openssl/archs/VC-WIN32/opensslconf.h
  /usr/local/include/node/openssl/archs/VC-WIN64A/opensslconf.h
  /usr/local/include/node/openssl/asn1.h
  /usr/local/include/node/openssl/asn1_mac.h
  /usr/local/include/node/openssl/asn1t.h
  /usr/local/include/node/openssl/bio.h
  /usr/local/include/node/openssl/blowfish.h
  /usr/local/include/node/openssl/bn.h
  /usr/local/include/node/openssl/buffer.h
  /usr/local/include/node/openssl/camellia.h
  /usr/local/include/node/openssl/cast.h
  /usr/local/include/node/openssl/cmac.h
  /usr/local/include/node/openssl/cms.h
  /usr/local/include/node/openssl/comp.h
  /usr/local/include/node/openssl/conf.h
  /usr/local/include/node/openssl/conf_api.h
  /usr/local/include/node/openssl/crypto.h
  /usr/local/include/node/openssl/des.h
  /usr/local/include/node/openssl/des_old.h
  /usr/local/include/node/openssl/dh.h
  /usr/local/include/node/openssl/dsa.h
  /usr/local/include/node/openssl/dso.h
  /usr/local/include/node/openssl/dtls1.h
  /usr/local/include/node/openssl/e_os2.h
  /usr/local/include/node/openssl/ebcdic.h
  /usr/local/include/node/openssl/ec.h
  /usr/local/include/node/openssl/ecdh.h
  /usr/local/include/node/openssl/ecdsa.h
  /usr/local/include/node/openssl/engine.h
  /usr/local/include/node/openssl/err.h
  /usr/local/include/node/openssl/evp.h
  /usr/local/include/node/openssl/hmac.h
  /usr/local/include/node/openssl/idea.h
  /usr/local/include/node/openssl/krb5_asn.h
  /usr/local/include/node/openssl/kssl.h
  /usr/local/include/node/openssl/lhash.h
  /usr/local/include/node/openssl/md4.h
  /usr/local/include/node/openssl/md5.h
  /usr/local/include/node/openssl/mdc2.h
  /usr/local/include/node/openssl/modes.h
  /usr/local/include/node/openssl/obj_mac.h
  /usr/local/include/node/openssl/objects.h
  /usr/local/include/node/openssl/ocsp.h
  /usr/local/include/node/openssl/opensslconf.h
  /usr/local/include/node/openssl/opensslv.h
  /usr/local/include/node/openssl/ossl_typ.h
  /usr/local/include/node/openssl/pem.h
  /usr/local/include/node/openssl/pem2.h
  /usr/local/include/node/openssl/pkcs12.h
  /usr/local/include/node/openssl/pkcs7.h
  /usr/local/include/node/openssl/pqueue.h
  /usr/local/include/node/openssl/rand.h
  /usr/local/include/node/openssl/rc2.h
  /usr/local/include/node/openssl/rc4.h
  /usr/local/include/node/openssl/ripemd.h
  /usr/local/include/node/openssl/rsa.h
  /usr/local/include/node/openssl/safestack.h
  /usr/local/include/node/openssl/seed.h
  /usr/local/include/node/openssl/sha.h
  /usr/local/include/node/openssl/srp.h
  /usr/local/include/node/openssl/srtp.h
  /usr/local/include/node/openssl/ssl.h
  /usr/local/include/node/openssl/ssl2.h
  /usr/local/include/node/openssl/ssl23.h
  /usr/local/include/node/openssl/ssl3.h
  /usr/local/include/node/openssl/stack.h
  /usr/local/include/node/openssl/symhacks.h
  /usr/local/include/node/openssl/tls1.h
  /usr/local/include/node/openssl/ts.h
  /usr/local/include/node/openssl/txt_db.h
  /usr/local/include/node/openssl/ui.h
  /usr/local/include/node/openssl/ui_compat.h
  /usr/local/include/node/openssl/whrlpool.h
  /usr/local/include/node/openssl/x509.h
  /usr/local/include/node/openssl/x509_vfy.h
  /usr/local/include/node/openssl/x509v3.h
  /usr/local/include/node/pthread-barrier.h
  /usr/local/include/node/pthread-fixes.h
  /usr/local/include/node/smalloc.h
  /usr/local/include/node/stdint-msvc2008.h
  /usr/local/include/node/tree.h
  /usr/local/include/node/uv-aix.h
  /usr/local/include/node/uv-bsd.h
  /usr/local/include/node/uv-darwin.h
  /usr/local/include/node/uv-errno.h
  /usr/local/include/node/uv-linux.h
  /usr/local/include/node/uv-os390.h
  /usr/local/include/node/uv-sunos.h
  /usr/local/include/node/uv-threadpool.h
  /usr/local/include/node/uv-unix.h
  /usr/local/include/node/uv-version.h
  /usr/local/include/node/uv-win.h
  /usr/local/include/node/uv.h
  /usr/local/include/node/v8-debug.h
  /usr/local/include/node/v8-experimental.h
  /usr/local/include/node/v8-platform.h
  /usr/local/include/node/v8-profiler.h
  /usr/local/include/node/v8-testing.h
  /usr/local/include/node/v8-util.h
  /usr/local/include/node/v8-version.h
  /usr/local/include/node/v8.h
  /usr/local/include/node/v8config.h
  /usr/local/include/node/v8stdint.h
  /usr/local/include/node/zconf.h
  /usr/local/include/node/zlib.h

Warning: /usr/bin occurs before /usr/local/bin
This means that system-provided programs will be used instead of those
provided by Homebrew. The following tools exist at both paths:
  git
  git-cvsserver
  git-shell
  git-upload-pack

Consider setting your PATH so that /usr/local/bin
occurs before /usr/bin. Here is a one-liner:
  echo 'export PATH="/usr/local/bin:$PATH"' >> ~/.bash_profile

Warning: Your Xcode (7.2.1) is outdated.
Please update to Xcode 8.2 (or delete it).
Xcode can be updated from the App Store.

Thank you,

N.