I suppose I should have referred to my squid.conf file for the SSL question of your's, Brad - I forgot a setting.
Adding the following single line to your squid.conf (you can put it after your http_port declaration) will get you the same wildcard configuration that Bart stated, but with a much better proxy server:
https_port 127.0.0.1:443 cert=/PATH_TO_CA_CERT/cacert.pem key=/PATH_TO_KEY/key.pem version=1
Note, that you'll need 2.5+ for this feature (I used squid-2.5.STABLE3-1rh_7x available via http://swelltech.com/support/updates/squid/7.x/RPMS/).
I wouldn't suggest using Pound either. Plus, Squid is well on it's way to handling multiple certs with this same type of setup. A good page to watch is http://squid.sourceforge.net/ssl/
Happy proxying!
