After trying so many things for so long, I decided simply wait for a very long time - and in fact I was able to boot in. One of the many problems (and the primary one ultimately) was that my IPMI on my SuperMicro board seems to conflict with the video card I have in the box...so it seems that the video output simply stops at random places during boot. That's why I had so many random "hangs"...it would randomly stop updating the video on my monitor during the boot process. Strange.
Well, wouldn't you know. I just started syncing some files via my newly minted smb rootshare and it is clearly using the cache drive. This is via the Unassigned Devices plugin method. Any clue why?