Well, yes your fears are somewhat justified, there is some work involved to set up and maintain a music server mainly. Its worth it though. It will totally change how you listen to and explore music.
Squeezebox Touch and squeezeserver on a computer of choice is the way to start. Add a 1.5 Gb or higher USB drive to rip to and another for backup. I like Seagate drives. They have been fast and reliable and the backup software that come loaded on them works well. Yes make sure you keep backups!!! Things can happen, especially at first.
Rip to lossless .wav using Windows Media Player for an easy PC ripping solution that works well. Just make sure you start the rip manually after all the metadata is set correctly. Don't use autorip or the first track will likely be missing metadata tags in the header and have to be redone to fix. Get the tags right the first time before ripping. If you think you will want or have to go back later and change or add metadata tags manually, use lossless .flac format for editable tags, not .wav.
That's the jist of it. Good luck.
