1. Not sure, cool idea though
2. Latest build have volume controls using the right thumbstick. Left is volume down, right is volume up.
3. Not sure if you want to randomize a playlist, aka shuffle it. If this is what you wanna do there is a setting in settings->music->shuffle playlist on load.
If you are trying to make a random playlist from all your songs each time your boot, that would most likely require a python script.
I have a playlist with all my Mp3s on it and just shuffle on load, works great
4. Not sure...
hope i helped a little, Nick