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. Of course, some people really enjoy the ritual of taking out a disc, putting it in a player and sitting down with the booklet.
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. You'll likely discover you have CDs that you haven't listened to in 9 years and not bother with them. It takes only a few clicks to start the ripping process, then you can walk away and come back anytime after it's done. Do those first, then the others as you have time. Even from a collection of 100's of CDs most of us listen to only a few dozen on a regular basis. 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. But you can say the same thing about CD player transports. Its not a matter of whether your hard drive will fail, its when. Hard drive space is so cheap now that there's no reason not to have multiple backups, preferably one off-site. Redundancy - Having your music on a hard drive and replicated to another drive with a regular backup strategy is great insurance. 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. Remote control - Being able to quickly choose and rearrange the order of what you're listening to from a phone or tablet. Sync it with an iPod and I can drive hundreds of miles without the distraction of shuffling CD's. The road trip playlist has almost 500 songs in it. 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.
Playlists - Creating your own playlists with selections from any of your tunes is interesting and useful. 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.
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