I think, maybe, we are talking about different things.
Exposing the myriad of OpenSSL library interfaces using CLFN's is not the same thing that you are describing. While multiple individual calls can be wrapped into a single wrapper function to be called by a CLFN (create a CTX, set it to a client, add the certificate store, add the bios then expose that as "InitClient" in a wrapper ... say). That is different to what you are describing and I would make a different argument.
I would, maybe, agree that a wrapper dynamic library would be useful for Linux but on Windows it's not really warranted. The issue I found with Linux was that the LabVIEW CLFN could not reliably load local libraries in the application directory in preference over global ones and global/local CTX instances were often sticky and confused. A C wrapper should be able to overcome that but I'm not relisting all the OpenSSL function calls in a wrapper.
However. The biggest issue with number of VI's overall isn't to wrap or not, it's build times and package creation times. It takes VIPM 2 hours to create an ECL package and I had to hack the underlying VIPM oglib library to do it that quickly. Once the package is built, however, it's not a problem. Installation with mass compile only takes a couple of minutes and impact on the users' build times is minimal.