I use an iMac to an Maudio Audiophile Firewire. That connects to my latest purchase, a Monarchy 24 DAC. Almarro A205A MK2 to Cain Abby/Baileys. I store my CD collection on an iomgea 750G hard drive.
I have never equaled this sound via any standard CD setup, and rarely has my vinyl surpassed it. The convenience factor is out of this world. I just hit random on my iTunes library, and I have the best radio station ever - all of MY favorite music. I hear things I had totally forgotten about. Songs I would have never pulled out of my LP collection. It's always a nice surprise.
I don't think I'm missing anything by using Apple's Lossless format. Even older (1986 vintage) CDs are listenable with this setup. No details are missing, and the music is engaging. Once one gets past traditional ways of storing and listening to music, life can get easier and better. Don't let anyone try to convince you that you are taking a backwards step in fidelity. If they haven't heard this setup, they shouldn't judge it. This is NOT like hooking up to an iPod or direct out of a computer's 3.5mm headphone output.
Go for it, and enjoy!