Random play order rules or guarentees

[OttoKerner]

Ability to "connect" songs in a playlist so they always play together

Those of us who like bands that transition seamlessly form one song to the next would love the ability to randomize a playlist, but it always separates those multi-song connected sections. It would be wonderful if there was a way to check a box or something next to songs in a playlist to tell Plex to always play these specific songs in this order, or always shuffle these connected songs together.