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Storage Limit Reached Issue

(I posted this in iOS a couple days ago. Figured I would post here too as this seems to be way more active and since I paid $150 for the software, perhaps there's a solution in here.....)

Having frequent issues on my wife's iPad. Either things won't sync or some other issue. I have 4 movies synced to it right now. Tried syncing 6 episodes of a TV show... Each show is 400-500MB and I had 17.6GB of space left. No issue right?

Wrong.... First, got a message "Storage Limit Reached"
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Closed Plex, reopened it and it appeared to be fixed.
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So, I selected the season of shows... 6 episodes of Dice (funny BTW). Synced them and then checked on status:
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So I deleted all 6 episodes and then figured I would try 1 episode. It worked fine.
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Then I tried the remaining 5. Did them one after the other. All 5 files in the Sync window were flickering back and forth between downloaded and queued . I can't paste a video unfortunately. Here are a couple screen grabs while it was flickering.
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So I deleted all of those to try again. My available storage ranges all over the place.... After a couple iPad hard resets, here's what I had.
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5 seconds later I had no space available.
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But according to the Sync Settings screen, I had plenty.
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So, I synced all 6 episodes individually and it worked. Surely this $150 software I bought can't be this complicated.

I bought this so my wife and kids had something easy to use. My wife refuses to use it now because every time she tries something is screwed up and not working. I searched the forums and found numerous threads up to a year old. Someone, anyone... please tell me this is being addressed. Surely it can't be this difficult.

FYI, I'm running iOS 9.35 and have the latest version of Plex on my iPad. I know this, because I deleted it an reinstalled 2 different times during all of this. I also deleted my wife's account and made her a new managed account just in case....


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