Idea for media player functionality

So, there are two ideas I had recently for media player functionality related to the shuffling function, and I was wondering about how feasible it would be to implement either/both.

First: Weighted Shuffling
Make a playlist, fill it with movies/TV shows, and apply weights for shuffling, so you can have movies play half as often, certain shows/episodes play more often, etc.
(this seems like it would be pretty easy)

Second: Conditional checks that change the playback order

Say it shuffles randomly to episode 1 of a show. (Possibly any show using filename checks for certain strings, like e01?)
You have an option checked where if it flips a coin and it comes up positive, it abandons shuffling and plays files in an order determined by the user when turning this option on, then when the list is run out, it goes back to shuffling.