Thanks for the detailed reply; I think it will help many others. What I am most concerned with today are those cases where the client does support the container/codecs and the media still wont play with the generic profile:
Unless there is some other problem with the video file, that should not happen. If your device can play the media files then it can, if it can't play that file it can't. It is the equivalent of double clicking your file to play it in windows. Having a profile isn't going to change that. All a profile is going to do is change what the server thinks your device can play, and from that if your profile can't play it then the server will try and transcode it to something that can. Adding a profile will not give your device extra capabilities, rather it is there to limit what gets sent to the device.
What about situations where a video plays in the Plex browser client, but does not play in the Plex native client, and it only plays on the DLNA TV from Serviio or Universal Media Server (not from PMS) ? Should I presume that Plex needs custom profiles for the TV and the native Plex client, or should I conclude that the server is buggy and wait for an update?
This has a lot so I will try not to jump around too much in a response.
The web manager already has profiles setup for browsers and for the most part is pretty limited to what can actually be directplayed.
Which Plex native client are you referring to as that makes a big difference? The client on LG's is "supported" (I believe it hit EoL as they no longer use it on new models) by LG directly, the new LG app for newer models is developed by a forum user, the Samsung App was started by a forum user and is maintained by him (I believe it hit its last update for older models recently), And all of those will behave differently from clients on the Android or Plex Home Theater.
Why it plays on one server vs another comes down to a lot. The most common difference I have seen is subtitles. Over DLNA the only way plex handles external srt files is by transcoding so if you try and enable the subtitles the server must transcode the file and if your on the generic profile the file gets sent without subtiles, if you have a custom profile the subtitles are sent burned into the video stream, if you have a custom profile that doesn't work correctly you get errors. The only difference I have seen has been with transcoded streams and in those I found UMS/Serviio to have extra options in their profiles that let me create profile that would transcode. Not that it was any easier, but the extra options did make it work. I actually had both a Plex and UMS server running side by side just to play transcoded streams to my LG until I bought a FireTV. After that I only run the Plex server because my PS3 works fine over DLNA, the FireTV uses the Android App, and on our PC's I use Plex Home Theater. But more specifically, you would have to start looking at the logs to figure out if it is a bug in the server or something else causing faulty playback. Just "It wont play" won't be enough for anyone to try and recreate or debug the issue.
If Plex has a bug, where should I report it? (I cannot find the bug tracker system).
This is going to vary. Since you keep mentioning the Native Plex App if it is a bug in the client (Which is more likely) it would be in the respective forum to that app, if it is in the server you can usually post in the server board for the OS you are using. Plex Ninja's will normally read the posts try some troubleshooting with you/request logs before sending the information to the developers. If you get a PlexPass there is also additional boards you could post on or check.
Why do software DLNA clients such as VLC and Windows Media Player not work with the Plex DLNA server, but do work with other media servers? Is this a known issue? Does it affect all Plex servers, or just some particular hardware & OS platforms?
Working with other media servers is relative. When I tried using WMP with my Twonky server it just gave me a list of every single video file on the drive. If I tried to select by folder it just called it a video folder and threw them all in there. Trying to find a specific video file in a list of 8,000 isn't working well in my opinion. I tried it with UMS and got the same thing as Plex "No files have been found on this remote library". Personally, I believe that if you want to use Plex I would look at Plex Home Theater or XBMC with PleXBMC add-on over VLC/WMP for DLNA content playback. Either option will give you full playback along with the all the artwork and structure that Plex provides.
If the generic profile causes the server to send everything, but media which my device can play is not being played, I am a little confused now about whether I should be trying to create a custom profile if it will not enable playback of media that already works on my clients when it comes from other media servers. Is there a comprehensive guide to configuring other server settings which might explain how to resolve these client compatibility issues?
You are going to be more specific. If you're using a Plex client (TV app or something) then it is already using it's own form of profile, most of which are built into the app itself. If your just using a DLNA browser from a TV and it is not playing, I would look at what profile your TV is using on the other server and see if it is indeed remuxing audio/container or something else which should also be visible in the logs.
But the it works on one thing but not another is not enough to try and diagnose the problem. If it is working on one server we would need to know what profile/settings/logs from the other server is using, the mediainfo for the file, how you are trying to play the file from plex (App/Dlna), and a log after trying to play the file from Plex where it isn't working.