Adrian - could you provide a little more information. What version of ArcGIS for Server are you using? And, is it a Basic, Standard or Advanced edition? This information will help determine the capabilities of your Server. Also, I really like Brian's suggestion to start by using ArcGIS Online and get some quick wins while you figure out how you want to use your Server license. Lots of smaller organizations and departments use Server Workgroup but there are some limitations, as Steve mentioned. Take a look at the ArcGIS for Server Functionality Matrix (a buyer's guide of sorts) and look at the Capacity section. In the mean time, look at the ArcGIS for Server (Windows) installation guide and the Portal for ArcGIS (Windows) installation guide. You might want to just try installing Server on your machine first to play around with it before you try to put it into production mode. You can always install and configure Portal later. Focus on the Single Machine Deployment for your test environment. Since you'll use the Server to generate web services, you should talk to your SysAdmin about testing a GIS Server on your machine. Definitely talk with Esri Support about what you want to do. You'll need to know your Esri customer number.
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