More than 5 months ago that in the iOS application there is a very annoying error, the songs in flac when playing them in wi-fi, the songs begin to be played in the second 5 (more or less) aunqe the application tells you that it is the 1 second.
when you use the 4G / 3G connection the problem is solved (I think the problem is related to transcoding)
tested with 3 devices with the latest version of plex media player 4.29:
iPhone 7 iOS 11.3.1
iPad 6 generation iOS 11.3
iPad mini 2 iOS 11.2.6
I tested with two different servers:
Intel NUC7I3BNH version 1.12.0.4829 / 1.13.0.5023
Raspberry Pi 3 version 1.10.1.4602
I have managed to download a version of the older plex application from iTunes, specifically version 4.15 does not have this problem, it may help you to investigate where the error comes from.