Hello,
What program should I use to RIP from a purchased audio cd? I want to make sure it is in a format that PLEX easily reads so I don’t have to do a lot of manual intervention. 
Any assistance is recommended.
Windows Media Player works just fine. Any MP3 ripping tool works. I would stick to the MP3 format for the best compatibility.
How about the naming convention that PLEX requires. Is Windows Media Player do the naming that PLEX reads easily?
Exact Audio Copy or XLD (X Lossless Decoder) for Mac. Use these if you want high quality results.
Most ripper software can be adjusted to use a Plex-compatible file and folder schema.
I know for certain that Exact Audio Copy can be adapted just fine.
I think that the main decision is “what is the codec that I will choose”. My ears can still hear the difference between loss and lossless codecs so I’ve chosen ALAC because all my playing devices (except my car) also accept it. I use iTunes to rip CD’s and dBpoweramp to convert some tracks to be used in the car (there are not many rippers around that support ALAC).
What still “plagues” my music experience with Plex is its lack of support for classic music tags and multiple artists per track, and the fact that I have to manually check and change lots of tags (specially genre) so that I can manage my music library.
