Randomize playlist in iTunes 11
Here's a walkthrough. I don't have a link to instructions somewhere because I haven't been able to find any, I figured this out a few days ago out of necessity.
in iTunes 11, enable the sidebar to make this easier (view -> Show Sidebar)
Here you can see my original "Demo" playlist that is clearly organized by track name.
First:
Create a new smart playlist (from file menu or from the + menu at the bottom left of the screen)
Second:
In the smart playlist options match on playlist, and select your original playlist
Third:
Select the "Limit to:" option, and put in a number that is AT LEAST the number of items on your original playlist (I just put in 99999). Make sure it is set to limit to items by random. Uncheck the "Match only" and "Live updating" options.
You will then have a new playlist that is a randomized version of your original
Optionally you can highlight all tracks, and then create a new regular playlist from them if you'd like to remove the "Smart List" (since smart lists based on other playlists don't work with icloud and itunes match)
I hope this helps anyone else that is having the shuffling problem. If you shuffle the list and then sync it to your iPhone/iPod then you can just leave the shuffle option on MFT off. MFT will play the list in the shuffled order that it was sync'd. I reshuffle my list every couple of weeks and resync it to the device. Has been working fine for me so far.