As mentioned above, Computeraudiophile.com is a great website for this.
I can realate to being overwhelmed by tech speak. I suggest starting simple, getting your feet wet, and then investing more. All this is evolving very fast, by the way, so not sure spending a lot in the latest DAC or server will be great 3 years down the road.
Are you familiar with the Apple environment or Windows? If Apple, I would say get a Mac Mini with iTunes and Audionirvana+ and that would be your server as starting point. If Windows, any PC or laptop will do to get started, and JRiver is a good option. I did the latter and I am now building a hotrod server.
Do you like your DAC? If so, keep it and get a good USB to S/PDIF converter, like an Audiophilleo. It has asynch USB (a good thing), and connects between your computer (be it Mini or Win based) and DAC. It's a connect it and forget it kind of thing, and works great. I also did this.
Ripping CDs is not trivial. I suggest following the Computeraudiophile guide to ripping CDs. ITunes is convenient, but not very good for this.
Generally speaking, storing music in an external hard drive with its own power supply (not usb powered) is a good idea, as well as avoiding using the USB connections for both streaming ( to the DAC or USB converter) and to access the music. So you want an external hard drive with a firewire, thunderbolt, or some other connection.
Will you be using an iPad or something as a "remote"?
Computer based has many moving parts, but can be executed rather simple. You will have plenty time to get a lot more complicated if you want, but leave that for later. At least this is the approach I have followed and worked great for me!