I'm seeing the same problem.   I have the Verison Messages App on my PC I was working fine until about 7/6/2019 then it stopped seeing 1) texts I sent from my phone and 2) incoming texts.  It wil still send texts.   

Just today 2/20/2019 I reinstalled the PC App (Version: 2.0.2.0).   It attempted to sync.  I see the same older messages as before.    (i.e. still broke)

(I'm using Android so I guess i will have to try Android messeges on my phone and PC.)