After 9 years, iTunes has left me beaten and broken

Since 2010, I've owned two iPod Touches and currently use an iPhone 7. All three worked fine OOTB, and I was able to sync 5000-10000 of my ALAC songs using the "Convert to lower bit rate" option. I did this by creating an "On" playlist on my PC for all the songs I want to sync to my device. For each device, this worked fine for some time, but each of them eventually became "poisoned," and syncing became unreliable. Some random, often changing set of songs would fail to sync, and current versions of iTunes do stupid things like deleting them from my playlist on my PC, ruining my playlist. Now I make backups of my playlist before syncing so I can recover from this bug. For my iPhone 7, I recently found that wifi syncing avoided this problem, and this worked fine until the latest release of iTunes, 12.10.0.7, which consistently cannot find the iPhone when it looks for it to start the sync. The dialog box "Looking for iPhone" appears for a while, and then the iPhone icon disappears from iTunes. Moreover, until it's restarted, iTunes doesn't detect the iPhone when I connect it with a cable. It's such a ridiculous mess.

So I've given up. I turned off the "Covert to lower bit rate" option and am syncing a smaller number of my ALAC files, on the order of 2000 or so. In my experiments with this, it has never failed, so we'll see how it goes. This is the reluctant culmination of nine years of frustration. I actually like iTunes quite a bit besides this, but the one job it had, it does miserably.

NB: This is not asking for suggestions on how to fix this. I'm past that. iTunes is fundamentally broken WRT my prior usage, and it's been broken for nine years. There's nothing a user can do to fix it. There's nothing a user did to break it.

P.S. I've commented before on these Apple forums that don't keep me logged in past a few days, then require 2 factor authentication, then require "trusting" the browser I've used all along. It just happened again. It's absurd.