I would say that the quality of the rip is first and foremost. Unless the drive or the CD itself is damaged, any modern drive should be able to achieve a perfect rip, so long as you are using good software, such as Missing Media Burner for Mac or EAC for Windows. However, I have extensively compared ripping results between Toast 6 and Missing Media Burner (using the "CD Paranoia" mode), and they turn up identical each time. The ripper in Toast 6 is damn good, really, and since it it is easy to use (GUI instead of Missing Media Burner's arcane command lines), I pretty much stick to Toast now for ripping.
The iTunes ripper (both Mac and PC versions) is crap, however. I would recommend you avoid it. It chokes on problem (scratched) discs, and cannot extract any tracks correctly, time-wise. It does weird things with the gaps between the tracks, etc.
We've all gotten hold of CD-Rs that won't burn correctly, etc. Of course I've gotten great results with very cheap CD-R media. Longevity is the real question. Most cheap media falls apart really quickly, even if you can get a perfect burn onto it.
I've been content sticking with TDK and Fuji CD-R's. They are widely available and relatively cheap. You can get a box of 50 TDK CD-R's with colored slim cases at Costco for less than $20. Yes, they are the "Made in Taiwan" ones, which so many people tell you to avoid. Why, I don't know. I've been using the Taiwanese TDK and Fuji discs for years now, and I've never had a Taiwanese TDK or Fuji go bad on me, not once.
If you love Hi-REZ TAPE HISS, you're REALLY going to love Stereo Central