Bart,
Welcome back - hope you had a good time!
No, I don't experience that problem. As an example:
http://www.kyoteproductions.com and
https://www.kyoteproductions.com
Both use the squid configuration outlined in this thread.
I put my cacert.pem in the ca directory of the server, and my key.pem in the modules/nsopenssl directory of the server. Perhaps you're experiencing a permissions problem?
I'd be interested in seeing the much-needed changes in Pound. Since I don't use SSL for any sites (but my own), and since I don't need to restrict SSL for certain parts of my site, the current configuration works fine.
If Pound is able to resolve the subsite SSL issues then I'll simply plug it in to the same configuration that I have with tinydns and be good to go.
As it is, the current configuration with Squid proxy is the most sound solution I've come across thus far.