When I rip my discs I always have the filename be <artist> - <album> - <track number> - <track title>. I use Exact Audio Copy for ripping since it's hands down the best. I then convert from the WAV to mp3 using BlueRazorLame and the latest LAME codec. Yes, I know I could convert directly using EAC but I don't. I like having more control when I use BlueRazorLame in a secondary step. Lastly, I quickly run the file through Dr. Tag which used to be a great program until the company was bought by someone else. Since it was bought about 3 years ago they pulled down the forums and there has not been a single update. Nonetheless, the older Dr. Tag 3.00.2 (build 172) which was a beta-type build works beautifully. It takes my already configured filenames and tags my mp3s with both ID3v1 and ID3v2 tags. Given the speed of my system I can have to fly through a lot of files very quickly.
I'm sure some will consider my method slow but it works for me and it really isn't as much work as it sounds. It takes me no time at all and with their being an Explorer shell-extension it's cake to tag entire folders & sub-folders.
I've tried other tagging software due to my great hatred toward the company that took over Dr. Tag development but at the end of the day I find myself returning to Dr. Tag because it's so easy and powerful and gets the job done with no extra effort.
Lastly, I know some people don't put the artist name and album title in their mp3 filenames but I do this because it means I can move files around and always know the exact file. I have all my music grouped in sub-directories from A to Z in terms of the artist name so each letter has it's own directory. I also have one directory that is 0-9 since I don't have many bands like that. I then have a sub-directory per artist name and sub-directories for each album from each artist. It makes keeping things organized easier and that is definitely needed with 120 GB of mp3s on a HDD.
Once you take care of tagging both foobar2000 and Winamp are both viable options. As I said earlier, Winamp is the easier of the two out-of-the-box. Foorbar2000 takes some more thinking. Both are very functional. With the right settings both sound very nice. Personally, I prefer the simplicity of foobar2000 and the only DSP I use is Resampler (PPHS).
Below is just how simple I have foobar2000 set up. I don't want to sit and stare at it so There's no need to make it all pretty.