I've sent you the logs per direct message.
That sounds like a cool setup. I'm just going to post replies in here as it's easier for me to keep track of everything plus I think it might help others troubleshoot their own problems in future.
So the 501 error was a red herring, it's trying to send a pause command but the device has already crashed with a 500 error so it's reporting the command was unsupported because it didn't get a response (I think....). Actually, looking at it again, I believe the stream is crashing the device and stopping playback and the plugin is then attempting to send the pause command in an attempt to sync playstates which I'm not 100% sure why yet but because it's already crashed it's reporting this error. I need to go over this but the issue is the stream is crashing the device.
For the most part it seems to be working, it's connecting, starting the stream and successfully setting the NextURI. So it's probably related to the WAV file. Its currently getting encoded to apply DSP/replaygain settings.
If you haven't already I would try the following
1. Make sure your firewall is not blocking anything.
2. check "Do not use raw PCM" and see how that goes, you should see L16 or L24 as the extension in the log instead of .WAV
3. If option 2 doesn't work, try and get it to play a native stream. Remove DSP/replaygain settings and adjust the profile to make sure it won't encode the file and see if that will stream ok.
You want the log to have "GetFile" entries, not "GetEncodedFile".
The more I look at that "Do not use Raw option" I feel like Lyrion had it backwards. Wouldn't L16/L24 be classed as RAW as it's just PCM? WAV is PCM with a 44 byte header although from what I've read it can contain other things, I don't know.
edit: Also I believe you can set upmpdcli to log to a file. That might give you a better idea of what's causing it to fail. The plugin error log isn't that great for solving problems as it doesn't know why the device did or didn't play something. The device log should give you more info in this regard.