No, Shuffle can be set per Type (Tools > Options > Playback Rules). However you can right click and use [url=https://www.mediamonkey.com/wiki/WebHelp:Playing_Audio_Tracks/5.0#More_Options_to_add_files_to_the_Playing_Queue]Play shuffled[/url] or Play Now in [url=https://www.mediamonkey.com/download]MediaMonkey 5[/url] to get the same effect. Play shuffled will add the files in a random order to the Playing.

That is a basic feature sorely lacking then!

I don't believe there is ... no

But if I am selecting songs from anywhere else.. I want it to shuffle.

I don't want to toggle "shuffle" on or off. Is there any way to make it understand the difference between selecting an album to play.. and any other situation!