Playlist shuffle always plays the same few songs

I got a playlist that has roughly 250 songs. Everytime I connect my Ipod to charge it, then disconnect and start the playlist on shuffle mode, there's always a 20 to 30 songs playing first. If I close my Ipod and start the playlist again (still on it most of the time), it shows 1 of 250 and plays the same songs, but not in the same exact order (though sometimes it does for 2 or 3 songs). Just like if the shuffle was on "low" mode or something. It's still choose randomly some song here and there, but not that much since it the same few, ALL THE TIME for a while. The only way to get around this is to connect my Ipod to my computer again (it reset it somehow) or leave it open all the time so it knows wich song has been played (but that's terribly stupid). Is there any other way to go around that shuffling loop? I found myself skipping most of the time since I always hear the same few songs even though there's some songs in the playlist I've never ever played on the Ipod. Is there a way to set the "priority" (like play the most higher rated song first) or the "intensity" (from low to high) of the shuffle?
Got the last 7th gen. Ipod Nano.

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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It pains me to hear about your experience with the Home Phone Connect. This device usually works seamlessly and is a great alternative to a landline phone. It sounds like we've done our fair share of work on your account here. I'm going to go ahead and send you a Private Message so that we can access your account and review any open tickets for you. I look forward to speaking with you.
TrevorC_VZW
Follow us on Twitter @VZWSupport

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Playlist shuffle always plays the same few songs

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