Music Tracks intermittantly skip

I love Plex and migrated my music from SubSonic to Plex to have my media all in one place. Problem I have, is the music side of things are not working properly.
I play a track fine, then I reload the browser and it sometimes skips the same track. And skips a whole heap more before finding one it likes to play.
I found this on Windows and the Linux Version. The tracks it doesn’t like appears random, so some will play sometimes and some won’t and vice versa.
SubSonic is looking like an attractive option again right now.

Things I’ve tried,

  1. Tried a different browser, I know some browsers render pages and handle traffic differently so tried all the usual ones, chrome, firefox, Edge and I even resorted to IE. As a left field I tried Opera as well.
  2. Checked the tracks format was compatible, it is, I have lossless Apple, MP3 and all are non DRM.
  3. Checked and triple checked permissions on the files, in both windows and linux. Made sure plex owns the files and has full rwx on the files.
  4. Tried installs of Plex on Windows(2012 R2, 2016) and Linux(Ubuntu). For the Windows I made sure I had the media packs installed so codecs were dealt with correctly.

Anyone had the same issues?

Also, the iTunes importer doesn’t work, neither does playing lossless tracks from the Cloud server either.

The last two Plex Server releases (1.5.5.3634 and the one before it) have caused some of my Flac files to get skipped while playing through the Roku 3. Has anyone else been experiencing this? I am running from a QNAP NAS to the Roku. It has worked for a long time. It just started showing up very recently.