Playlist "Shuffle" refresh methodology?

Hi All,
Does anyone know when iTunes will refresh the playlist's shuffle content?
For example, If I add:
Song A - Artist A
Song B - Artist B
Song C - Artist B
Into the play list they will always stay like that... However on the bottom of the playlist in iTunes we have access to a shuffle icon, by doing such, it will reoganize the music to be something like:
Song C - Artist B
Song A - Artist A
Song B - Artist B
And seems to stay that way...
However If I now drag
Song D - Artist C
Into the list, and maybe a few others, it once again seems to stay this way... However if I manually cycle the shuffle icon, the songs will once again re-arrange.
Is there any way to get it so that this list will indeed keep shuffling? Or is it already, but I'm not aware of it's refresh process... Such as it will reshuffle the songs once played through the list in iTunes?
As one of the reasons why I am asking is iTunes the Nike+ feature on my Nano... So I set the time, and choose my cardio play list... But one of the songs continually grows in its play count because its the first one when I chose it.... If I add shuffle then it seems to re-arrange the list, but again I only add songs normally to the playlist in iTunes and play most of the time through my iPod.
So what I'm trying to get here is a diverse startup process to the songs so that my playlist somewhat moderates and I additionally get a diversity to which song I'm going to hear first.
Thoughts? or advice???

On the iPod's Now Playing screen, there is a Shuffle button. The symbol looks like two arrows crossing. Is that set to ON?
I ask this because shuffing a playlist should NOT always put the same 20-30 songs at the top of the list. Shuffle means a randomly ordered list is created and played. If the original playlist is in a somewhat random playlist order to begin with, playing it in play-in-order mode may seem like it is shuffling, even though the iPod is playing the list in playlist order. And the same songs would be at the top of the list every time, because the iPod not shuffling the list.
Sorry if that's too basic, but I need to ask the obvious question first, and that question is, IS is the iPod actually set to shuffle songs?

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Playlist "Shuffle" refresh methodology?

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