iTunes skipping songs in Playlists

As of today, iTunes has started skipping playing certain songs in my iTunes library and playlists. These could be songs purchased or converted from CDs, it seems no pattern. On all tracks I can click get info, read all information on the track, browse to the folder the track is in and all is fine. Typically in a playlist of 60-70 songs it will play maybe 10 tracks.

If I click the track directly from the folder to play, it wont. All songs have numerous plays in the past and been working fine. I dont want to rebuild the playlists if possible as some are 300 songs+ that have accumulated over years. The files themselves seem fine but just wont play. I have also updated iTunes to latest version and checked the drive for errors but all is ok.