Being an Open Source guy software licencing always sounds iffy. There are though all these software licencing giants - they must be doing something right. The model hinges on selling using rights to the nuggety core code and surrounding it with a halo of hyped marketing and some very good service.
Oracle licences stuff per core with funny multipliers for diffrent CPU vendors, before the acquisition People Soft used to licence its product my a magic company valuation formula. The stock prices should have been set by how much a company's PeopleSoft licence costs.
Most vendors except the largest ones use a 3rd party licencing tool like FlexNet, whose older versions are very weak. The fixed number of licence idea be it attached to cores or to users creates an artificial ceiling which may halt production. In the financial industry the solution to limited cash is credits be it over drafts in cash accounts or margin lending for share trading. Since software licences are just as ephemeral and dynamic in value as currency, and most licence servers have extensive usage statistics measurements - software licencing should be fuzzy.
Fuzzy software licencing means degrading performance e.g. code efficiency and available runtime reduction when licences are overdrawn. If the financials can be sorted then an intermediate point to the Software as Service (SAS) model - bills are generated for extra usage.
Scalability in any process is always an issue, but with economics being like the weather maintaining operations at full scale is not feasible. May be the idea of pop-up shops will catch on.