I don't like headset, out of home (I work at home) listen to the gray noise -- so I use an old Pioneer sx-626 with homemade loudspeakers (and only two, no 5.1-like tricks); usually playing from laptop, what is my portable at the same time onboard audio or playing from pc through an old fashioned Terratec soundcard.
Fileformats: only ogg (q7-9 vbr), mpc, mp3 (in this order). Lossless are converted because of diskspace -- never write cd or dvd (what are so interesting in quality, has bought the original).
Progs are mostly Winamp (2.8) and Amarok; after tryed and used a couple of ripper I stand at CDex 1.5 for ripping, also for converting, and medieval cue splitter for splitting -- never editing, if a file is wrong, than wrong -> F8. I didn't find the last for clear junk data, repearing wrong headers. Tagging (after a lot of searching, trying) only with Mp3tag.
Tag (and other over-hyper-meta) data are from "manual" search only (if no cd/lp-cover at hand), always checking more sources, if available.
Controlling and monitoring with Total cmd and its lister...