I was in the same position as you and went with itunes as I am happy with the sound quality and ease of use. If you have a mac, itunes is literally built for it. When you import any CDs do so with Apple Lossless to get the best results. Therafter what you do depends on whether you can tell the difference between lossless and lower bit rate files.
It is odd that the Womad store sells downloads at Apple Lossless, but itunes is still limited to 256kbps AAC files. I am quitehappy with itunes AAC downloads, but if I really pay attention, with some music I can tell lossless files are better. There is a greater clarity and depth to the music.
I would certainly look to using your mac as the source rather than getting a Brennan. The Brennan is rated well, but it limits you to certain files and file sizes more than the mac does. With a mac you can also access online music services and radio. Mac connected to a DAC to an amp to speakers or headphones will give you access to a massive and wonderful world music, potentially without a CD in site. That is how I have done it. I am presently listening to Peter Gabriel and The Fun Lovin' Criminal's new albums online, for free. My CDs live in the loft.