I would look into the Bryston BDP-1 or BDP-2.
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I use a Mac mini with pure music as my main player, feeding it into the Jolida Dac Transport. Prior to upgrading to the Jolida, I used an Arcam Rdac, and was very happy with it. The Arcam is relatively cheap, you can find them somewhere in the neighborhood of $300, and you definitely get your money's worth.
Running a headless Mojo Mac Mini into a PS Audio Directstream DAC, playing from iTunes through PureMusic. No CD transport at all. (It works well unless my cable provider craps out, as I just recently had happen.)
I'd suggest hanging an external disc off the MacBook Pro to store your library. This allows you to easily clone your library disc to another disc for safe storage. Plus, you won't get contention on the internal drive between system functions and serving music. Or, NAS is an option.
+1 on checking the Empirical Audio site. That's where I got started. You may also find good info at places like Amarra.
To your first question - yes, using a properly set up computer system with an external hard drive and good quality DAC has significant advantages over playing CDs.
Playlists - Creating your own playlists with selections from any of your tunes is interesting and useful. I have playlists of all kinds, a road trip list, a dinner music list, a girl singers singing sad songs list, a list of my daughter's favorite music to play in the background at her wedding rehearsal dinner. The road trip playlist has almost 500 songs in it. Sync it with an iPod and I can drive hundreds of miles without the distraction of shuffling CD's.
Remote control - Being able to quickly choose and rearrange the order of what you're listening to from a phone or tablet.
Streaming - It's simple to play music as you're describing on your main system and simultaneously stream it to secondary systems like an office or workshop.
Redundancy - Having your music on a hard drive and replicated to another drive with a regular backup strategy is great insurance. Hard drive space is so cheap now that there's no reason not to have multiple backups, preferably one off-site. I have at least three. Its not a matter of whether your hard drive will fail, its when. But you can say the same thing about CD player transports.
One of the concerns about doing the kind of change you're describing is the time it takes to rip a large CD collection but for me it was pretty painless. Even from a collection of 100's of CDs most of us listen to only a few dozen on a regular basis. Do those first, then the others as you have time. It takes only a few clicks to start the ripping process, then you can walk away and come back anytime after it's done. You'll likely discover you have CDs that you haven't listened to in 9 years and not bother with them. Even if you ever do want to listen to them again you just put them into the optical drive on the MacBook and play them directly, and you can be ripping them at the same time.
Of course, some people really enjoy the ritual of taking out a disc, putting it in a player and sitting down with the booklet. I enjoy that, too, but having a system like the one youre describing opens up all kinds of possibilities that will change the way you enjoy the music, for the better in my experience.
One last thing - As with all things audio its easy to become obsessed with every detail involved in the sometimes highly technical aspects of setting up such a system. My experience is that starting simply with a decent DAC, maybe driving it from the optical output from your Macbook, makes the learning curve simpler and lets you upgrade as you learn more.