Most of my music is uploaded from CD's, originally using an Apple internal drive, and now using an external Blu-Ray, DVD, CD drive. Simple.
Getting the artwork is spotty. I'm not sure why. Some is there. Some isn't. Some used to be, and isn't.
One unsolicited suggestion. If storage space isn't a problem, and especially if you are playing to a good sound system, upload uncompressed, or losslessly compressed music. You can put the stuff in smaller formats on your portable devices. Apple lossless has always worked fine for me.