Besides ArcMap connections what else counts toward the 10 user limit with workgroup? If I have multiple webapps, arcgisonline, and collector using data coming from ArcGIS server, does that count as one connections or does each app hitting the service count as one? I'm trying to justify upgrading to enterprise, I only have 5 arcmap license but plan to deploy more web based viewers, apps, portal, etc.
In terms of connections, it depends on the number of processes initiated by ArcGIS Server web-services (besides connections created from ArcMap users). Each process from a service would create a concurrent user connection. The Pooling & Isolation parameters of the service regulate this phenomenon. More connections would be created to the database if more users access the apps consuming these services simultaneously.