A few months ago I was in a position similar to yours, having no experience with streaming music at all.
Visiting a dealer I noticed how convenient streaming could be, with an ipad and a NAC 272. I could see an advantage in reducing the number of cd's in our living room as well, and decided to get myself a streamer.
On the internet I found a s/h ND5SX at a reasonable price. So I had to do all the setup myself. I can assure you that setting up a basic solution is very easy. I did it like this:
ND5SX was connected to router (with standard ethernet cable, wifi also possible) and to AUX on amp. Now internet radio was working. Downloaded Naim app from app store. Then with windows media player I ripped some cd's to wav files on a USB memory stick. This I inserted on the front of the ND5SX and the files were immediately available for streaming.
This is all it takes to get started. I used this setup for about a month.
Next, I added a basic NAS drive, 2 TB Seagate Personal Cloud (100£). Connecting to pc and setup was simple, following the included setup guide. When connected to the router the NAS drive automatically showed up on the ND5 (when selecting UPnP input), and I could stream the music from the NAS.
Nothing so far should be too complicated to do yourself, and a setup like this is (IMHO) a very good place to start.
After this you may want to fine tune things. Going for a higher spec NAS, changing server software to Minimserver or Asset, install a dedicated cd ripping program, change ethernet cabling etc. etc. And optimize use of metadata info (artist, year etc) on your music files. Of course, the more you get right in the first place, the less you'll have to change things later. But that also makes it more complex to get started.
There are many things you can do to tweak the setup, and reading on these pages about all the options could make things sound more complicated than they are/have to be.