I will address the music question first, as that is what I am most familiar with.
Yes, you can randomize the music you play from folders, but it takes creating a playlist first that pulls out individual tracks. You copy the playlist(s) to the internal drive or external drive connected to the media player. The player has a “shuffle” mode but it is not that good of a shuffler; especially when my entire iTunes library with 1000’s of tracks is involved…
It’s best to create a playlist of random tracks to play, although one can shuffle that playlist via the media player, too. During the year I have had my Live Plus unit I have strove to create a truly random list using either iTunes or Windows 7 media player. Both had their shortcomings, and it was not until recently that I stumbled upon the “holy grail” method of creating truly random playlists.
This is how I do it today:
All my iTunes media files are on an HD connected to the media player; basically it is the backup of my iTunes Media folder, with more than just music in it. (Movie videos are on a second attached HD, so the media player knows where to look for the music and always goes to the correct drive.) So, all 9000+ tracks of music are there, and it is a selected list I created by making a “Smart” playlist in iTunes so only the music I want to play is in there, minus Podcasts and videos, as well as any artist, album, etc. I don’t want in there is absent. This is the music I listen to on my iPod on shuffle mode and also what I want to hear via the media player.
Here is where the random playlist begins; from the Smart Library I have set up. This is what I discovered recently to make the random playlists. I select the music from this Smart playlist and have "iTunes DJ " instantly select tracks from it. DJ can be set to pull up to 100 tracks. This random playlist is exported (saved) to a playlist file called iTunesDJ. I add the #1 to the name, hit the refresh button and another 100-track playlist is created, and I add #2 to the name of this list. I make a few of these as it only takes a second, and copy them all to the drive with the music into a folder called Playlists and the media player finds this folder and displays all the playlists in it.
I play through these playlists, and when they are used up, I can easily create new random ones. Hopefully, this is enough info to help anyone to also do this.
Photos? I don’t use that feature much, but perhaps iTunes or Win 7 media player can create photo playlists as well for the media player, too. Maybe someone who does this can step in next and tell us how.