iTunes playlist trick needed


Okay, I`m sure I`m dating myself here, but it`s safer than dating anyone else.

I have this thing I want to do with a playlist on my iPhone and in iTunes on my desktop so that it sounds like the only radio station I grew up listening to in the 60`s. I have all the airchecks I need from CKLW Windsor and the Big 8 Jocks from 1964 on, and I need to figure out how to get them in there every two or three songs so they don`t clump together and play one after another, which would sound pretty weird and ruin the effect.

All I can think of is to edit the airchecks into the start or end of certain songs, or number everything on the list and turn off shuffle...

Shuffle won't work to do this so far on my desktop, so I'm stumped right now.

Any other ideas?


In Geostationary Orbit
How do you have iTunes payback set in iTunes Preferences? Is Crossfade turned on and set to short?