On the static issue, I had rebuilt some extensions out of curiosity to see what kind of size increase we would be seeing, and there were some ridiculous size gains in some of the ones I built. Openssh.tcz grew from about 888kb to 4.6mb. That is over a five fold increase and I saw some other similar increases in other extensions, though none as much as openssh.tcz since is so tightly dependent on openssl. Of course, it would not be such a big deal if an extension grew by a megabyte-ish, but it is each binary or library that will grow that is ssl dependent.
Given this, I contacted some of our main extension makers and so far the agreement is unanimous that a shared build of openssl is overall advantageous. I should have looked deeper into this earlier, but it will be seamless to update the openssl-1.0.0 extension to be shared. It simply means that once about every 3 years we will deprecate the current openssl into a libssl extension for legacy extension support. And three years is enough time to migrate from one version to another, but with the libssl extension availability there is still no pressure in that regard.
I will rebuild the openssl-1.0.0 extension to be shared and no changes on the part of extension makers or users is required. Thanks everyone for your patience.