The ripping and the metadata issues are separate. You certainly want to get the best rip you can. Ripping isn't fun, doing it once is ok, doing it again isn't. I ripped a few albums with iTunes many years ago, and the results were patchy, but that was many many versions ago. I used EAC which is free, configurable, but rather hard work. I now use dbpoweramp and once set up its pretty much perfect. I originally ripped to multiple formats, but I now just use FLAC, as dbpoweramp can convert between formats quickly and efficiently if I ever need something else. I convert to MP3s for the car or portable devices, but have given up on iPod/iPad/Phone music, except for holidays. 320k MP3s are pretty good though!
My main PC is an iMac, but I run a windows server with Dbpoweramp, TVersity and Logitech Media Server on it, mainly so I can run Dbpoweramp.
Metadata is another issue entirely. Dbpoweramp does the best job that I have found in finding the info, but the classical stuff still ends up in a mess. I generally hand edit each classical album, but I've got a huge backlog to fix. One day I'll find or write a program that will batch edit them the way I want them. The fact that many classical albums can have multiple composers, orchestras and conductors on one album makes life very difficult, but the one big pleasure with streaming is the fact I can listen to my favourite classical piece without the horror of some totally inappropriate filler track killing the moment after the glorious finale...