I believe it is concurrent connections, so you could have 10 users setup but only 5 would be legal to use it at any one time - sure someone will correct me if this is wrong.
Basically as many as you like as only 5 people are allowed to log into your server at any one time.
It's basically all down to simultaneous connections rather than number of "users" you setup on the server.
So, you take a Server 2003 with 5 CAL's.
You have 100 users setup on the server all with Roaming Profiles.
Only the first 5 simultaneous connections are legal - as soon as you hit number six you're running illegally.
However there should be nothing stopping you physically setting up any number of users as you are only actually breaking your license agreement once more connections are being made than you own CAL's.
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