How do I prevent iTunes Match from causing songs to disappear from my playlist on Mac and iPhone?

Itunes Match keeps causing hundreds of songs to disappear from my playlist both on my Mac and on my Iphone. Even a senior Apple support specialist who was viewing my phone and computer at the time said he's never seen this happen and could not help. I have had YEARS of problems syncing my playlists from first my PC then my MacBook pro to my iphone. I have been on the phone dozens of times with apple support. Once a certain problem is solved, another comes up. It used to be that all the songs I burned from CDs or bought as MP3s on other music services like Amazon would not show up at all on my laptop or Iphone. Other times, half my playlist would disapear when itunes or IOS had an update.

However, twice now the latest problem is that when an Apple support specilalist on the phone, who I have enabled to see my iphone and computer are watching - they tell me to try Itunes match. Both times as they watched, as soon as it turned on, hundreds of songs just disapeared from my playlist both on my phone and my Mac. Its super annoying.

I keep having to recreate my playists from almost scratch. The songs themselves are on my phone and Mac - just NOT on my playlist, or if they are on my playlist, they move all the way to the end, and thus are totally out of order. This just happened today when a senior iPhone and Mac specialist was on the phone with me. I was having my usual trouble syncing my iTunes playlist from my Mac Pro 16 inch purchased in 2024, which has all the latest iOS and everything else including the latest version of iTunes, to my iPhone. My iPhone also has all the latest everything. It's an iPhone 16 Max Pro. Anyway, he said to leave this message with Apple Support because he's never seen this happen before. Basically, even though I've previously had all kinds of trouble with iTunes match when another support person had told me to turn it on to help sync my playlist I went against my better judgment and listen to this guy and turned it back on. Sure enough, as he was watching both on my phone and on my Mac he saw multiple songs just disappear from the playlist on both my Mac and iPhone. Which is exactly what it happened last time. What made this so annoying was that after the last several times my iTunes playlist had multiple songs disappear, each time for a slightly different reason as I mentioned above, I've had to spend hours re-creating the playlist from scratch. I had told him all of this before we turned iTunes match back on and sure enough I'm now gonna have to do it again. Again this is a senior Apple Support specialist who says he's baffled and has never seen this happened and he apologized. I was on the phone for 90 minutes with two different Apple Support people today. And now my playlist is worse than it was before because iTunes match made multiple songs that I purchased using my current Apple ID via iTunes as well as songs that I've burned from CDs or songs I've burned from other services disappear completely from my playlist. What's more these songs are still in my library both on my phone and my Mac. They just are not on my playlist.

So the problem is, I constantly cannot sync my playlist from my old PC and now from my Mac to my various iPhones, but on top of that iTunes match, which is supposed to help with this, instead makes songs completely disappear for my playlist, but not for my library. I doubt anyone has any solution to this when two separate Mac and iPhone specialist from Apple could not solve this problem. But the guy urge me to put this online, hoping that somehow someone in Apple would know how to fix this.

[Re-Titled by Moderator]