Can iTunes do this somehow?

Hi. This is another question for my Internet Radio Station at school

Next year, we will be expanding our programming schedule to include a total of 90 minutes of programming a day. The plan is to play those programs over again twice after school, then switch to a random shuffling of a playlist until the next program.

Can this be done with iTunes? Is there an automator task or an Applescript or something to do this with? If not, is there any other software that will do it? When I say "Other Software" I mean below $300 MAX.

OK. I created an automator workflow which sucessfully makes the switch from the playlist to iTunes DJ. The question is: how can I schedule it to occur at (for example) 9:45 every day (except on weekends)?

Ah. The answer lies in a little piece of Shareware called Daypart. Nice little tool that lets you schedule out a whole day of playlists if you want to.