I don't use NetBSD, so perhaps I'm not in "the loop", and please forgive me if so, but;
- GCC 5.5 is only one major version higher than the oldest supported version; 6 or 7 would have been a better choice while you're banging out a whole new operating system release, 6 is still fully supported, 8 was released early this year. I understand newer compilers can sometimes introduce regressions in the build process for something as large as an entire operating system, but surely they could have tested it and gotten those bugs fixed if any?
- Similarly for Clang/LLVM 3.8.1 (Really? The oldest version of Clang that you can get on a modern Linux distro? Really?).
- OpenSSL 1.0.2 is only supported for another 17 months, 1.0.2k (the version they're shipping) is 3 versions older than the current 1.0.2o, and 1.0.2p is going to be released any day now. There are at least 4 CVEs patched between 1.0.2k and 1.0.2o; I hope they're applying those patches on top of 1.0.2k manually.