There's no way to have to auto-advance through the songs and skip certain ones. However if you're playing individual songs, you could set up & use song Metadata to filter out songs any way you like and choose another one from the filtered list.
Yes. There's a Song Metadata feature built in, but requires code to do anything with the Metadata. There's an example on the documentation website. You wouldn't manipulate the Playlist at runtime, you would set up the metadata for each song ahead of time, then use code to find your song and play it.