Definitely start ripping your collection now. Take a look at DB Poweramp before you do though, seriously. I started out with just EAC, and sure do wish I would have used DB from the beginning. Something as mundane as album art can really turn into a nightmare later. I've tried numerous album art finding programs to only give up and live with no album art for the majority of my collection.
PS Audio makes some pretty killer audio gear, including stand alone DAC's. They also make a music server worth a look. Not as expensive as the Olive products, but not cheap either. They took a different approach than Olive by not incorporating an internal hard drive or CD ripper. You just plug your Ext hard drive into it, or your network and it does the rest. I'm actually quite intrigued by this device.....
http://www.psaudio.com/ps/products/description/perfectwave-dac?cat=audio
