NOTE: We use a wildcard SSL certificate which makes our life much easier when dealing with multiple hostnames. I have not tested this approach with multiple SSL certificates for specific sites.
We’ve been reconfiguring our SharePoint 2007 farm over the past couple of days and it’s now hosted on Windows Server 2008 and using NLB (network load balancing). The load balancer has been configured with a single public IP address and all our previous DNS CNAME registrations have been replaced with hostname A registrations pointing at the address. With our previous configuration we had multiple IP addresses on the server, one for each web application. Each IIS web site was then configured with a host header and ip address to allow for secure traffic over HTTPS.