WIndows 10 sync not working with IOS again!!!!!

[mghou]

Plan

Premium

Country

US 

Device

XR and Tablet

Operating System

Windows 10

IOS 12.1.4 

My Question or Issue

Sometime in January I noticed that many of my local songs had gone missing from my playlists yet again.  Not only have I uninstalled/reinstalled all of the clients, checked firewall rules, etc,  none of the ones that used to sync (and are now greyed out) plus new local file based playlists will not come over either.  

On both of the phone and tablet I see where it tries to "download" 58 of the missing files but it never makes it over.  I am definitely on the same wifi network.  When I got a new phone this week (which means completely new phone install too) same behavior.

This is more than frustrating/crazy.  I will be looking for other options to get my local files on my phones (including Apple music).   It really should not be this hard.

What else can I try????