How to connect a flash drive to a VMware VM when the drive is 'not readable'?
Re-install VMWare. You may need to go to your Mac's System Preferences-&gt;Security &amp; Privacy-&gt;General and allow VMWare permissions in the 'Allow apps downloaded from:' section.
For reference I updated to the following versions and I was able to get my flash drive to show up inside of my VM:

Catalina v10.15.5
VMWare Fusion v11.5.5