Streaming Radio with playlist injection?

[DarkArtist69]

Untimely i am wanting to stream music from my server through VLC but have the ability to play IDs, certain music clips, at certain time and ads as well.
For example. 10 songs would play and it would play an ID then ten more songs and it would play an ID and an ad. is there a way i can have it play a folder of music, randomly then inject these other music clips, possible from another folder, after a number of songs have played?

Does that make sense. i have tried looking for this but am unsure what to even look for.

I had thought if i could create playlist from folders but when the folder content was changed it would change the playlist but i dont like VLC will do it that.

Any help will be appreciated.
Thank you

[RogerRamjet]

DA: I have personally developed a co-brand version of my Promusic.fm internet radio website for radio stations to add their logo and use our ad server for audio/synced banner ads and promo IDs. Listeners can create their own playlists by selecting any combination of artists. If you'd like a demo let me know and I'll set up an account for you to try. There is no charge to you for this. We pay all Sound Exchange and performance licenses. I make my money by selling ProPlay packages to indie artists.

Roger