With the single core limitation, caching with ArcGIS for Desktop is only intended for cache with limited extend and/or level, such as a local government and study area. For more exhaustive cache (e.g. North America from L0 to L18), ArcGIS for Server is the recommended approach.
In regards to monitor the process, beside keeping an eye on the created files' date in Windows Explorer, you can also use the Status.gdb to get addtional feedback on your caching progress. Please note that you won't be able to see this file geodatabase inside ArcMap/ArcCatalog unless you copy it to a location other then the cache folder. More specifically:
Spatial information about the completion of map cache tiles is
contained in the Status.gdb file geodatabase in each cache folder. You
can make a copy of this geodatabase in another directory and open its
feature classes in ArcMap to see tables and maps of map cache
completion status. The TaskStatus feature class is especially useful
for seeing the tile bundle boundaries.