Why not C89? Try to make it as portable as possible. The software is intended for preservation of old computers and their software. Would make sense for the software to be as portable as possible.
Who knows, maybe someone would want to run it on vintage Mac hardware?
This is a good point. For a while, I was writing vintage Mac hacking tools in ANSI C [1].
The answer is that it's too hard. I want to see the Happy Mac on as much exotic hardware as possible, but my day job keeps me very busy, and I want to enjoy my hobby without tedium and toil. I prefer to use a language that is "easier to write, easier to read, easier to understand, easier to maintain" [2].
It already exists. But, if any, Free Pascal with Lazarus for classic Mac ppc would be ideal.
Put that MacSSL port available under fpc and now you can compete with the rest.