Question : Hosting multiple web sites on one physical server

I have a design issue that I need to understand before coming up with a strategy, regarding hosting mutliple web sites.

I use both Apache and IIS (mostly IIS) and would like to host multiple sites on one physical server.  I will have a mixture of HTTP-only sites and HTTPS sites.  

I've heard that you can host multiple sites on one server via host headers, but that technique may be incompatible with some browsers.  So to get around this, you can configure the server with multiple IP addresses on the same subnet, but can run out of IP addresses.

I've also heard that if you host multiple sites that require SSL, you need to go with multiple IP addresses on the server.  BUT, as I understand it, the SSL cert is "bound" by the common name or FQDN of the site.  If I host multiple sites for a single customer/domain name...will I need to consider host headers or multiple IP addresses on a single server?

Also, want implications or "gotchas" do I need to take into consideration if I have a wildcard certificate?

Any help in best practices, resources, whitepapers. or anyone's experience would be greatly appreciated.

Answer : Hosting multiple web sites on one physical server

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