That sounds about right. The last iTunes was a mess. I’m not happy with Music so far. It seems like it’s formatted around Apple Music streaming cloud stuff? I don’t use it. So it isn’t very user friendly for me. Not quite intuitive like i like Apple products to be.
I agree about Classics being the ideal music platform and own two aging 160s. Based on all I've read here about Catalina problems and music messes in particular, I'm sticking with Mojave, but bit the bullet, buying a 256GB iPod Touch several months ago. I love it.
My music collection was pushing the 148GB actual capacity of the Classics and with vanished Apple support for them, I got the Touch and no longer need worry about Classics failure or maxing out the 148GB.
The Touch on IOS 13 lacks favorite Classic iTunes features such as Genius Mixes and regretttably the Click Wheel, but it's current hardware technology, good for future expansion, and Bluetooths with my Alexa devices, my TaoTronics noise canceling earphones and my iTonics hearing aids. A Touch will probably sync with your Merc, and two way control possibly. If you can afford a Merc, you can afford a Touch, they really are neat machines and a very useful Classic replacement.
iTunes/IOS on the Touch also has some features the Classics don't, like "Recently Added" on the menu, and you can always add your own playlists to make up for the lost Genius Mixes. It does have a versatile playlists capability along with the many other Touch applications like Maps for navigating your Merc.
Sometimes you have to accept that Apple doesn't really give a s*** about their long time customers that supported them when Jobs was on holiday playing with his own Next toy company, and the Cook/Beats/Dr. Dre administration began the rapid skid down the software QC slope and the departure of any new ideas, the Jobs "one more thing", thing.
I've been an Apple supporter since the Apple II in the mid '80s, owning dozens of Mac and associated hardware, and am no longer surprised to find new wiggles, good for their major profit line, the iPhone, accompanied by indifference to user support of other devices.
They are taking reasonable care of IOS because their monthly evolving iPhone/iPad lines need it, but obviously have a different, less capable crew working on the Catalina mess, so the future of the Touch looks solid.