Yes. The EPDM API includes hooks for many different events including check in and check out. An addin (C#, VB, C++) can be written to generate a PDF (by opening SolidWorks) in response to any of these events.
This is probably also possible with the Dispatch API, but I prefer to use addins.
The simple way to do it would be from the the Work Flows.
To do it automatically, set an automatic state transition with a convert pdf task attached to it.