I'll answer each bullet-point separately from above:
If you are using a CAL model, you DO need a CAL for every distinct end-user or device that accesses your server (there is both a user-CAL model and a device-CAL model)
If you are asking if there is a way to basically dynamically/programatically increase the number of CALs assigned to your server, the answer is no. There actually is no license-management tool at all with Sql Server 2005+ (so far) - the license management model is a model called 'integrity' (i.e. you are responsible for being an ethical user of the software and properly licensing the server). This can be a bit different if you have a software-assurance or enterprise-agreement with Microsoft, but it's basically the same.
I was the one who answered it on StackOverflow - what this means is that you need a user or device CAL license for either every distinct user OR every distinct device (i.e. laptop, computer, server, phone, etc.). In a web-facing environment (i.e. you have a website exposed to the internet, or to hundreds/thousands of users on an intranet), you would need a CAL for every single user or device that accessed your web site. The CALs are NOT tied to the web-servers themselves, they would need to be tied to the end-users of the website(s) in question (this is called multiplexing and in no way reduces the number of CALs required for licensing properly).
In this case, you DO need 11 CALs, however the server will not explicitly force this upon you (see the answer to #2 above, this is the integrity part).
That should cover each question I hope. Note that in terms of #3, if you are using a website that is exposed to the internet and/or a large number of users/devices (large being likely anything in excess of ~20 in this case), you likely want to research the processor licensing model instead. A few good references for Sql licensing:
