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Plex Media Server issues

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Hi,
I've been running Plex probably 6 or 7 years now. I've always been a big fan of it, but I've always found little annoyances that really bother me. Typically simple things that just don't seem to work or give me an inconsistent behavior. After running very old versions of both the server and the client, about a month ago I updated everything to the latest and great and purchased Plex pass since it was only $75 since I've been a member for so long. Now I run Plex Media Server (2.6.1) and Plex Media Player (1.1.1) on a MAC Mini that is running OS X 10.11 which i believe is the latest, I had to upgrade that in order to upgrade PMS/PMP.

After the initial rebuild and upgrade of all applications, for the most part things seemed to be operating well. I was happy with the upgrade, the look of the new Plex server and player was awesome, nice and clean. After running for about a month or so, once again there are a few small simple things that have me just about ready to abandon the Plex ship all together because i'm frustrated. I am hoping that someone on this forum might be able to help me get these issues fixed otherwise i'm going to start moving towards alternatives.

Issue #1: New movies are currently not being added to Plex Media Server. I added about 6 new movies to an existing movie directory on an external hard drive that is part of my Movies library. After running an "Update Library" the new titles are not visible or available for playback. I've rebooted PMS and the mac multiple times, it doesn't seem to help. I've ran an Analyze, a Refresh All, and multiple update library's against my movies library and it just wont detect the new titles.

Issue #2. Manually updating Poster and Background images inside of Plex Media Server. I have a few movies that are not scraping their posters, or some i'd like to choose an alternative image. Every time I go to Choose an Image, Drag and Drop, or enter a URL I get "there was an error uploading this artwork - try again" or "Your Changes Could Not Be Saved." I know this worked on previous versions of server, why is it not working now. I've got local artwork stored in the same directory as the movie title, I've tried jpeg, bmp, I've tried grabbing URLs from the internet. Whatever i try to do it appears to fail. I only have 1 account on my Mac and one account in Plex, as far as I can tell both should have full access to the entire system including the external drives as attached storage.

I have turned the debug log up to verbose on Plex Media Server but I do not know how to read it. I could paste it in here but it's lengthy amount of text so i'm not sure if there is any benefit to what's in there.

These both seem to be pretty simple things but in the little bit of googling I've done it sounds like other people have seen these issues some people have not found resolution. Are these bugs or are these issues with my setup? In all honesty i'm seriously starting to look at Kodi as a potential alternative solution because frankly I just don't have the time to screw around with this anymore, I need something that just works.

If anyone has any tips I would appreciate the help.
Thanks

Update: all my movies are basically in a directory \Movies\Title (Year) format.


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