Ok, I'll be happy for it to be an installation problem... I just did a fresh install of the latest PlexPass release (.19) on a Mac running the latest OSX (laptop is running an i7, 16GB, and lightly loaded). I've also tried this on a Win8 machine as well with the same results, but its easier for me to work on the Mac.
Using the latest Shoutcast plug-in, I get the following in the Plex Media Server log. The messages are essentially the same regardless of using iOS, Android or Web based clients. And I've tried this both at the office and at home with similar results.
Apr 01, 2013 12:36:36 [0xb0185000] DEBUG - Request: GET /music/:/transcode/generic.mp3?format=mp3&audioCodec=libmp3lame&audioBitrate=256&url=http%3A%2F%2F127.0.0.1%3A32400%2Fmusic%2Fshoutcast%2F%3A%2Ffunction%2FPlayAudio.mp3%3Ffunction_args%3DY2VyZWFsMQoxCmRpY3QKMQpzNzcKaHR0cDovL3lwLnNob3V0Y2FzdC5jb20vc2Jpbi90dW5laW4tc3RhdGlvbi5wbHM%2540aWQ9MTQxMjQwOSZrPXNoMXQ3aHluM0toMGpobFZzMwp1cmxyMAo_&session=4DA1F911-6592-44D8-BB0B-AB5BCBAE592D&X-Plex-Client-Capabilities=protocols%3Dhttp-live-streaming%2Chttp-mp4-streaming%2Chttp-streaming-video%2Chttp-streaming-video-720p%2Chttp-mp4-video%2Chttp-mp4-video-720p%3BvideoDecoders%3Dh264%7Bprofile%3Ahigh%26resolution%3A1080%26level%3A41%7D%3BaudioDecoders%3Dmp3%2Caac%7Bbitrate%3A160000%7D&X-Plex-Device=iPhone&X-Plex-Token=KezsW7JFARfpox9cSZ9J&X-Plex-Client-Platform=iOS&X-Plex-Device-Name=Garry%20M.%20Paxinos%E2%80%99s%20iPhone%205&X-Plex-Model=5%2C1&X-Plex-Platform=iOS&X-Plex-Client-Identifier=4DA1F911-6592-44D8-BB0B-AB5BCBAE592D&X-Plex-Product=Plex%2FiOS&X-Plex-Platform-Version=6.1.3&X-Plex-Version=3.1.1 [172.16.105.83:59440] (1 live)
Apr 01, 2013 12:36:36 [0xb0185000] DEBUG - * format => mp3
Apr 01, 2013 12:36:36 [0xb0185000] DEBUG - * audioCodec => libmp3lame
Apr 01, 2013 12:36:36 [0xb0185000] DEBUG - * audioBitrate => 256
Apr 01, 2013 12:36:36 [0xb0185000] DEBUG - * url => http://127.0.0.1:32400/music/shoutcast/:/function/PlayAudio.mp3?function_args=Y2VyZWFsMQoxCmRpY3QKMQpzNzcKaHR0cDovL3lwLnNob3V0Y2FzdC5jb20vc2Jpbi90dW5laW4tc3RhdGlvbi5wbHM%40aWQ9MTQxMjQwOSZrPXNoMXQ3aHluM0toMGpobFZzMwp1cmxyMAo_
Apr 01, 2013 12:36:36 [0xb0185000] DEBUG - * session => 4DA1F911-6592-44D8-BB0B-AB5BCBAE592D
Apr 01, 2013 12:36:36 [0xb0185000] DEBUG - * X-Plex-Client-Capabilities => protocols=http-live-streaming,http-mp4-streaming,http-streaming-video,http-streaming-video-720p,http-mp4-video,http-mp4-video-720p;videoDecoders=h264{profile:high&resolution:1080&level:41};audioDecoders=mp3,aac{bitrate:160000}
Apr 01, 2013 12:36:36 [0xb0185000] DEBUG - * X-Plex-Device => iPhone
Apr 01, 2013 12:36:36 [0xb0185000] DEBUG - * X-Plex-Token => KezsW7JFARfpox9cSZ9J
Apr 01, 2013 12:36:36 [0xb0185000] DEBUG - * X-Plex-Client-Platform => iOS
Apr 01, 2013 12:36:36 [0xb0185000] DEBUG - * X-Plex-Device-Name => Garry M. Paxinos’s iPhone 5
Apr 01, 2013 12:36:36 [0xb0185000] DEBUG - * X-Plex-Model => 5,1
Apr 01, 2013 12:36:36 [0xb0185000] DEBUG - * X-Plex-Platform => iOS
Apr 01, 2013 12:36:36 [0xb0185000] DEBUG - * X-Plex-Client-Identifier => 4DA1F911-6592-44D8-BB0B-AB5BCBAE592D
Apr 01, 2013 12:36:36 [0xb0185000] DEBUG - * X-Plex-Product => Plex/iOS
Apr 01, 2013 12:36:36 [0xb0185000] DEBUG - * X-Plex-Platform-Version => 6.1.3
Apr 01, 2013 12:36:36 [0xb0185000] DEBUG - * X-Plex-Version => 3.1.1
Apr 01, 2013 12:36:36 [0xb0185000] VERBOSE - [IDLE] Adding (0->1) work item transcoder - 4DA1F911-6592-44D8-BB0B-AB5BCBAE592D
Apr 01, 2013 12:36:36 [0xb0185000] VERBOSE - [IDLE] Server is now active
Apr 01, 2013 12:36:36 [0xb0185000] VERBOSE - [IDLE] * transcoder - 4DA1F911-6592-44D8-BB0B-AB5BCBAE592D - 1 active item(s)
Apr 01, 2013 12:36:36 [0xb0185000] DEBUG - Cleaning directory for session 4DA1F911-6592-44D8-BB0B-AB5BCBAE592D (/var/folders/53/rxs_s65d6jg7crxgjq88gmm80000gn/T/plex-transcode-4DA1F911-6592-44D8-BB0B-AB5BCBAE592D-154c39b1-99d0-4977-8b99-7d65495a9519)
Apr 01, 2013 12:36:36 [0xb0185000] DEBUG - Starting a transcode session 4DA1F911-6592-44D8-BB0B-AB5BCBAE592D at offset -1.0 (stopped=1)
Apr 01, 2013 12:36:36 [0xb0185000] VERBOSE - [Event] Firing plex.event.transcodesessionmanager.sessionstarted to 0 sink(s)
Apr 01, 2013 12:36:36 [0xb0185000] DEBUG - Job running: /Applications/Plex Media Server.app/Contents/Resources/Plex Transcoder -i http://127.0.0.1:32400/music/shoutcast/:/function/PlayAudio.mp3?function_args=Y2VyZWFsMQoxCmRpY3QKMQpzNzcKaHR0cDovL3lwLnNob3V0Y2FzdC5jb20vc2Jpbi90dW5laW4tc3RhdGlvbi5wbHM%40aWQ9MTQxMjQwOSZrPXNoMXQ3aHluM0toMGpobFZzMwp1cmxyMAo_ -async 1 -f mp3 -acodec libmp3lame -ar 48000 -ab 256k -ac 2 -threads 0 -
Apr 01, 2013 12:36:36 [0xb0185000] DEBUG - Started session successfully, now saving it: 4DA1F911-6592-44D8-BB0B-AB5BCBAE592D
Apr 01, 2013 12:36:36 [0xb071b000] DEBUG - Started generic transcode output thread
Apr 01, 2013 12:36:36 [0xb0185000] VERBOSE - [IDLE] Adding (0->1) work item http_download - /music/:/transcode/generic.mp3?format=mp3&audioCodec=libmp3lame&audioBitrate=256&url=http%3A%2F%2F127.0.0.1%3A32400%2Fmusic%2Fshoutcast%2F%3A%2Ffunction%2FPlayAudio.mp3%3Ffunction_args%3DY2VyZWFsMQoxCmRpY3QKMQpzNzcKaHR0cDovL3lwLnNob3V0Y2FzdC5jb20vc2Jpbi90dW5laW4tc3RhdGlvbi5wbHM%2540aWQ9MTQxMjQwOSZrPXNoMXQ3aHluM0toMGpobFZzMwp1cmxyMAo_&session=4DA1F911-6592-44D8-BB0B-AB5BCBAE592D&X-Plex-Client-Capabilities=protocols%3Dhttp-live-streaming%2Chttp-mp4-streaming%2Chttp-streaming-video%2Chttp-streaming-video-720p%2Chttp-mp4-video%2Chttp-mp4-video-720p%3BvideoDecoders%3Dh264%7Bprofile%3Ahigh%26resolution%3A1080%26level%3A41%7D%3BaudioDecoders%3Dmp3%2Caac%7Bbitrate%3A160000%7D&X-Plex-Device=iPhone&X-Plex-Token=KezsW7JFARfpox9cSZ9J&X-Plex-Client-Platform=iOS&X-Plex-Device-Name=Garry%20M.%20Paxinos%E2%80%99s%20iPhone%205&X-Plex-Model=5%2C1&X-Plex-Platform=iOS&X-Plex-Client-Identifier=4DA1F911-6592-44D8-BB0B-AB5BCBAE592D&X-Plex-Product=Plex%2FiOS&X-Plex-Platform-Version=6.1.3&X-Plex-Version=3.1.1
Apr 01, 2013 12:36:36 [0xb0185000] VERBOSE - [IDLE] * http_download - /music/:/transcode/generic.mp3?format=mp3&audioCodec=libmp3lame&audioBitrate=256&url=http%3A%2F%2F127.0.0.1%3A32400%2Fmusic%2Fshoutcast%2F%3A%2Ffunction%2FPlayAudio.mp3%3Ffunction_args%3DY2VyZWFsMQoxCmRpY3QKMQpzNzcKaHR0cDovL3lwLnNob3V0Y2FzdC5jb20vc2Jpbi90dW5laW4tc3RhdGlvbi5wbHM%2540aWQ9MTQxMjQwOSZrPXNoMXQ3aHluM0toMGpobFZzMwp1cmxyMAo_&session=4DA1F911-6592-44D8-BB0B-AB5BCBAE592D&X-Plex-Client-Capabilities=protocols%3Dhttp-live-streaming%2Chttp-mp4-streaming%2Chttp-streaming-video%2Chttp-streaming-video-720p%2Chttp-mp4-video%2Chttp-mp4-video-720p%3BvideoDecoders%3Dh264%7Bprofile%3Ahigh%26resolution%3A1080%26level%3A41%7D%3BaudioDecoders%3Dmp3%2Caac%7Bbitrate%3A160000%7D&X-Plex-Device=iPhone&X-Plex-Token=KezsW7JFARfpox9cSZ9J&X-Plex-Client-Platform=iOS&X-Plex-Device-Name=Garry%20M.%20Paxinos%E2%80%99s%20iPhone%205&X-Plex-Model=5%2C1&X-Plex-Platform=iOS&X-Plex-Client-Identifier=4DA1F911-6592-44D8-BB0B-AB5BCBAE592D&X-Plex-Product=Plex%2FiOS&X-Plex-Platform-Version=6.1.3&X-Plex-Version=3.1.1 - 1 active item(s)
Apr 01, 2013 12:36:36 [0xb0185000] VERBOSE - [IDLE] * transcoder - 4DA1F911-6592-44D8-BB0B-AB5BCBAE592D - 1 active item(s)
Apr 01, 2013 12:36:36 [0xb081f000] DEBUG - [TranscodeOutputStream] Input processing thread started at offset 0 for -1 bytes.
Apr 01, 2013 12:36:36 [0xb0185000] VERBOSE - Completed request: GET /music/:/transcode/generic.mp3?format=mp3&audioCodec=libmp3lame&audioBitrate=256&url=http%3A%2F%2F127.0.0.1%3A32400%2Fmusic%2Fshoutcast%2F%3A%2Ffunction%2FPlayAudio.mp3%3Ffunction_args%3DY2VyZWFsMQoxCmRpY3QKMQpzNzcKaHR0cDovL3lwLnNob3V0Y2FzdC5jb20vc2Jpbi90dW5laW4tc3RhdGlvbi5wbHM%2540aWQ9MTQxMjQwOSZrPXNoMXQ3aHluM0toMGpobFZzMwp1cmxyMAo_&session=4DA1F911-6592-44D8-BB0B-AB5BCBAE592D: -2
Apr 01, 2013 12:36:36 [0xb0081000] DEBUG - Request: GET /music/shoutcast/:/function/PlayAudio.mp3?function_args=Y2VyZWFsMQoxCmRpY3QKMQpzNzcKaHR0cDovL3lwLnNob3V0Y2FzdC5jb20vc2Jpbi90dW5laW4tc3RhdGlvbi5wbHM%40aWQ9MTQxMjQwOSZrPXNoMXQ3aHluM0toMGpobFZzMwp1cmxyMAo_ [127.0.0.1:60672] (2 live)
Apr 01, 2013 12:36:36 [0xb0081000] DEBUG - * function_args => Y2VyZWFsMQoxCmRpY3QKMQpzNzcKaHR0cDovL3lwLnNob3V0Y2FzdC5jb20vc2Jpbi90dW5laW4tc3RhdGlvbi5wbHM@aWQ9MTQxMjQwOSZrPXNoMXQ3aHluM0toMGpobFZzMwp1cmxyMAo_
Apr 01, 2013 12:36:36 [0xb0081000] DEBUG - Plug-in com.plexapp.plugins.shoutcast has been used 86 times.
Apr 01, 2013 12:36:36 [0xb0081000] DEBUG - [com.plexapp.plugins.shoutcast] Sending command over HTTP (GET): /music/shoutcast/:/function/PlayAudio.mp3?function_args=Y2VyZWFsMQoxCmRpY3QKMQpzNzcKaHR0cDovL3lwLnNob3V0Y2FzdC5jb20vc2Jpbi90dW5laW4tc3RhdGlvbi5wbHM%40aWQ9MTQxMjQwOSZrPXNoMXQ3aHluM0toMGpobFZzMwp1cmxyMAo_
Apr 01, 2013 12:36:36 [0xb0081000] DEBUG - HTTP requesting to: http://127.0.0.1:59896/music/shoutcast/:/function/PlayAudio.mp3?function_args=Y2VyZWFsMQoxCmRpY3QKMQpzNzcKaHR0cDovL3lwLnNob3V0Y2FzdC5jb20vc2Jpbi90dW5laW4tc3RhdGlvbi5wbHM%40aWQ9MTQxMjQwOSZrPXNoMXQ3aHluM0toMGpobFZzMwp1cmxyMAo_
Apr 01, 2013 12:36:36 [0xb0081000] DEBUG - [com.plexapp.plugins.shoutcast] HTTP reply status 302, with 0 bytes of content.
Apr 01, 2013 12:36:36 [0xb0081000] VERBOSE - Completed request: GET /music/shoutcast/:/function/PlayAudio.mp3?function_args=Y2VyZWFsMQoxCmRpY3QKMQpzNzcKaHR0cDovL3lwLnNob3V0Y2FzdC5jb20vc2Jpbi90dW5laW4tc3RhdGlvbi5wbHM%40aWQ9MTQxMjQwOSZrPXNoMXQ3aHluM0toMGpobFZzMwp1cmxyMAo_: 302
Apr 01, 2013 12:36:36 [0xb071b000] DEBUG - Generic transcode session finished reading output.
Apr 01, 2013 12:36:36 [0xb071b000] DEBUG - Finished generic transcode output thread
Apr 01, 2013 12:36:36 [0xb071b000] DEBUG - Notifying stream that data is complete.
Apr 01, 2013 12:36:36 [0xb081f000] DEBUG - [TranscodeOutputStream] Input processing thread exited after writing 0 bytes, m_closed=0, m_endOfFileReached=1, session->isStopped()=0
Apr 01, 2013 12:36:36 [0xb040f000] DEBUG - [TranscodeOutputStream] Reached end of file
Apr 01, 2013 12:36:36 [0xb040f000] VERBOSE - [TranscodeOutputStream] Told to teardown
Apr 01, 2013 12:36:36 [0xb040f000] DEBUG - Removed transcode output stream 0x42a7400, active count 1 => 0
Apr 01, 2013 12:36:36 [0xb040f000] VERBOSE - [IDLE] Removing (1->0) work item http_download - /music/:/transcode/generic.mp3?format=mp3&audioCodec=libmp3lame&audioBitrate=256&url=http%3A%2F%2F127.0.0.1%3A32400%2Fmusic%2Fshoutcast%2F%3A%2Ffunction%2FPlayAudio.mp3%3Ffunction_args%3DY2VyZWFsMQoxCmRpY3QKMQpzNzcKaHR0cDovL3lwLnNob3V0Y2FzdC5jb20vc2Jpbi90dW5laW4tc3RhdGlvbi5wbHM%2540aWQ9MTQxMjQwOSZrPXNoMXQ3aHluM0toMGpobFZzMwp1cmxyMAo_&session=4DA1F911-6592-44D8-BB0B-AB5BCBAE592D&X-Plex-Client-Capabilities=protocols%3Dhttp-live-streaming%2Chttp-mp4-streaming%2Chttp-streaming-video%2Chttp-streaming-video-720p%2Chttp-mp4-video%2Chttp-mp4-video-720p%3BvideoDecoders%3Dh264%7Bprofile%3Ahigh%26resolution%3A1080%26level%3A41%7D%3BaudioDecoders%3Dmp3%2Caac%7Bbitrate%3A160000%7D&X-Plex-Device=iPhone&X-Plex-Token=KezsW7JFARfpox9cSZ9J&X-Plex-Client-Platform=iOS&X-Plex-Device-Name=Garry%20M.%20Paxinos%E2%80%99s%20iPhone%205&X-Plex-Model=5%2C1&X-Plex-Platform=iOS&X-Plex-Client-Identifier=4DA1F911-6592-44D8-BB0B-AB5BCBAE592D&X-Plex-Product=Plex%2FiOS&X-Plex-Platform-Version=6.1.3&X-Plex-Version=3.1.1
Apr 01, 2013 12:36:36 [0xb040f000] VERBOSE - [IDLE] * transcoder - 4DA1F911-6592-44D8-BB0B-AB5BCBAE592D - 1 active item(s)
Apr 01, 2013 12:36:42 [0xb09a5000] DEBUG - Shutting down idle session 4DA1F911-6592-44D8-BB0B-AB5BCBAE592D (idle time is 180 seconds)
Apr 01, 2013 12:36:42 [0xb09a5000] DEBUG - Stopping transcode session 4DA1F911-6592-44D8-BB0B-AB5BCBAE592D
Apr 01, 2013 12:36:42 [0xb09a5000] DEBUG - Killing job.
Apr 01, 2013 12:36:42 [0xb09a5000] DEBUG - Signalling job ID 22878 with 9
Apr 01, 2013 12:36:42 [0xb09a5000] DEBUG - Cleaning directory for session 4DA1F911-6592-44D8-BB0B-AB5BCBAE592D (/var/folders/53/rxs_s65d6jg7crxgjq88gmm80000gn/T/plex-transcode-4DA1F911-6592-44D8-BB0B-AB5BCBAE592D-154c39b1-99d0-4977-8b99-7d65495a9519)
Apr 01, 2013 12:36:42 [0xb09a5000] VERBOSE - [IDLE] Removing (1->0) work item transcoder - 4DA1F911-6592-44D8-BB0B-AB5BCBAE592D
Apr 01, 2013 12:36:42 [0xb09a5000] VERBOSE - [IDLE] Server is now idle
Apr 01, 2013 12:36:42 [0xb09a5000] VERBOSE - [Event] Firing plex.event.transcodesessionmanager.idle to 0 sink(s)
Apr 01, 2013 12:36:42 [0xb09a5000] DEBUG - Whacked session, 0 remaining.
Apr 01, 2013 12:36:42 [0xb09a5000] DEBUG - Killed 1 idle sessions, and 0 remain.