You can't make even a "big" iPod (that has a screen) do something that specific. :) In fact, I can't think of a way to make iTunes on your computer do that...
You can select a specific playlist to play (using VoiceOver), and play that specific playlist in playlist order (as seen in iTunes) or in random order (shuffle). It will continuously repeat that playlist until you stop it. Or, you can play all of your songs (not based on playlists) from the All Songs list.
Edit: Actually, you CAN do it for a specific case, if you create a new playlist where the songs from one playlist repeat four times, followed by the songs from the other playlists. In other words, you can create a playlist with any songs in any order, and sync it to the shuffle. Songs can appear on one playlist more than once, and on multiple playlists. iTunes only stores a song file once on the shuffle, even if it appears multiple times on playlists, so it won't take up any more storage space.