You've had lots of great advice on hardware and client software so I'll just toss in my two cents on ripping. I use
dbpoweramp reference ($36). It has a couple of huge advantages over most everything else I've used. The main advantage is a fully automated ripping. Setup properly it will not only rip your CD but will also look up the album information and tag your rips completely automatically. It will then file your rips away using your rules. In other words all you have to do is keep feeding it CDs and it does all the work. They also include a batch ripper should you have multiple CD drives.
Then once you've ripped your entire collection to a lossless format (FLAC?) you can run a MP3 batch conversion against your entire library. Depending on your settings it can create a whole new directory tree naming and tagging the files and filing them according to your rules in your favored bit rate for your portable - all while you have a beer and watch the game. The best part is it's idiot simple.
Well worth $36 to me.
For what it's worth I use a 4GB RAID5 NAS box to feed a Western Digital TV Live in the family room and another in my master bedroom. I store my music collection and rips of my concert DVD collection on the NAS and back up the music and DVDs to external drives attached to the WD's. The only disadvantage I've found to the WDTV Live is that you have to manually create play lists from your PC if you want to queue up multiple albums.
Also for what it's worth, when I had a PC plugged directly into my receiver I used WinAmp and one of the little tiny smart phone sized Lenovo micro HTPC keyboards for a remote.
