Windows voidtools.com everything.exe x64 is a tool that I use many Many times a day.  On days/nights that I DJ I might use it 100 times a 4-hour session. 

 

My hope is that I can setup everything.exe on the media shares live or with prescanned file lists.efu like I use with the drobo5N

 

Another program I use is MediaMonkey.com's Gold Product where I can also drag and drop tunes from the file lists to Virtual DJ, RadioBOSS, or SAM where I can drag and drop songs from the other apps into the internet radio programs.  I use different program depending on the venue, I need to use the same thing that the local DJs are using.

 

Now, it will take some tweaking, but I would like to do all of this on the same box with unraid, the mini-itx system with a 2600k and 16GB of memory, I has access to a pair of 240GB ssds, if I can use one for cache and one for a windows vm that's what I'll do.

It sounds like you will want to run a windows VM, doing a quick internet search the processor doesn't support VT-d. You can make sure here https://lime-technology.com/wiki/index.php/UnRAID_Manual_6#Virtualization_Host_2

 

If I was wrong and you system can support VM's, you will want to start your search here, there's a large amount of video's that will walk you through the process. Gridrunner has put a huge amount of work into these and have help many new Unraiders' through the process.

As long as your hardware is up to par, and you virtualize you should be able to have everything you want.