I've been attempting to cache a bunch of map services on 10.1 for a few weeks now. Some complete in one shot, others take several attempts and even then, I'm not sure if they are complete or not. The Caching status dialogue has yet to show results that give any confidence. The "job Status" tab on the Cache Status details dialogue has jobs that are "processing" even though the servers aren't doing anything and I can't seem to cancel them. I've attempted to run the "manage map server cache status" tool with no success (even though the tool reports "success" after completing). After running that tool, I get "0.0% of the tiles are present" even though I can view the service in the JavaScript viewer and see that there tiles present. I can even open the status.gdb fgdb and get all kinds of info. Is it reliable?
I'm very excited about where AGS 10.1 is going but wow, caching in 10.1 is like herding very temperamental cats. You can view/manage caching related activities from the service itself (by right clicking the service in catalog), going to the "server" tools in catalog or interacting (to a certain extent) with the service in the web based manager. There are tools for caching and reporting on caching and there are are services that do the same. You can run the jobs synchronously (same as "wait for job completion"?) or asynchronously (why not just always async?) report status via map service, or not (I haven't figured that one out yet). Each avenue has different UIs, capabilities, inputs, outputs, etc.
Any insight into this tricky caching business would be helpful. I've read through most (I think) of the online documentation but even then, there are enough "notes", "tips", "caution" and "legacy" statements that honestly it's hard to keep track of what the best path is.
Also, it would be great to see what bugs have been reported/accepted but I can't seem to find any esri pages for that. Esri, didn't you open that up a year or so ago?