Back when I first got CDs, I was very disappointed in the 'sound'... while many were touting the 'digital quality', I was hearing the imaging artifacts of the digitization and conversion back to analog, that took away the clarity of crash cymbals and tight low-end attack... and the quantization taking away dynamic range. Of course, when one rips an LP or other analog source to 33,100, the 15,050hz clarity is the first thing to go... but if you're driving around in a car, having a turntable mounted in the glovebox didn't become a 'popular' option, you had to pick 8-track or cassette (for disco, or rock, respectively) and if you were a hard-core audiophile or a deadhead, you had an Akai GX-280D in the back seat, so you could listen to either Wagner's Flight of the Valkyries, or the GD's Playing In The Band (which you drove your Microbus to Seattle to record live)...
Did I digress? Yeah... back to boats...
Most 'low quality' digital complaints are the result of someone taking a sound source and rastering it down to a digital format that is LESS than 44.1khz sample rate, and a very poor data bitrate... and most people don't know WHAT to listen for to hear it.
I have all my CD collection (and all my LPs, 45's, 8-tracks and cassettes... and some wax tubes...) ripped to MP3 format. I run 192kbps bitrate, which is significantly HIGHER in data density than an average audio CD, so the imaging errors are VERY hard to hear. If I'm in the boat, Burt Bacharach sounds just as good from a thumb-drive, as it did on the 8-track. but without the nasty BUZZ-CaChunk as the tape player shifted track and direction mid-song (yeah, I edited that out).
As for MrsRobinson's collection... do this- PM me a list of some the CD artist/albums that you HAVE... I'll send you a sample of what they sound like in a good-quality rendering. As others have noted, it is not difficult to get several hundred ALBUMS on a thumb drive nowdays, and once in that format, modern marine stereos handle that quantity of music, without requiring the physical space (or fragility) of a suitcase full of plastic disks.
Ripping them all to files onto a thumb-drive takes a little time, but as everyone has noted, a laptop computer nowdays will hammer that out fast, we can find a way to get it done.