That's what I've been doing with Audacity...FLAC and a copy in MP3 320 kbps. For Earbud type listening. I've been using Exact Audio Copy for the rip but again, just getting going. I will absolutely check out Foobar...using WinAmp for listening...although Win Media has an appealing sound at times...I'm curious how things might tie together with a quality CD player. Have only surfaced the DAC the computer may have...but that's on my mind too...how to improve the DAC, or is it unnecessary.
Just my two cents, but, once you have a ripper and a file format, you are pretty much good to go. EAC is pretty good. Consider that once you have an "exact audio copy" of a CD, how much more can you expect? Other rippers won't improve the rip. Once you get one that's spot on, your journey is pretty much done. Unless you don't like the UI on EAC.
Formats are pretty much the same. If you are doing FLAC you're pretty much home free. Its got all the CD info in it and other formats won't improve on that (unless you want WAV containers).
Players are another area people squak about but I'm not sure there is much of a difference there either. It falls in to the category if you like the sound of one player better than another, well, you've found your player. I've tried 3 or 4 players and don't sense much of a difference using the same files. YMMV, have fun sifting through them.
DACs are a non-topic for most of us. A DAC is designed to be sonically invisible. If a DAC is doing its job properly, its just moving bits. No sonic imprint, no sound changing. A $200 DAC will do the same job as a $2000 DAC. The DAC in my Mac Mini has been carrying the load and it doesn't even have a name.
This entire topic is YMMV when it comes to what you think you hear. If you like something better than another option, ride that horse.