What you suggest can be easily accomplished for about $2,300.
Get an Apple iMac
($799), an Apogee Mini-Dac
($850 street price) and two OWC Mercury Elite
180Gb firewire hard disk ($340). The iMac will run the iTunes software, the Apogee has a USB I/O and a high quality DAC to connect to your preamp and a single 180Gb HD will store up to 300 CDs (use the 2nd HD as a backup drive).
Hook up the iMac with an internet connection, start the supplied iTunes software and place a CD in the CD-ROM tray. Within 3-5 minutes the CD will be ripped onto your HD with the album info/song titles info. It will take you maybe 20 hours to fully rip 300 CDs. Once completed the iMac does not require an internet connection. iTunes has the ability to make multiple playlist so you will have enormous control over what music you want to hear. The sound quality will be approximately equal to a high end stand alone CD player.