@andy.mehalick Not sure this will help you, but I was able to get my Meadow to update and get the HelloWorld app up-and-running. For me what seemed to dislodge whatever was going on was running the meadow download os command. After that my Meadow started communicating on COM4 (no idea why) and I had to run a few other commands and that got everything up-to-date that I could deploy the app from Visual Studio.
NOTE: I did have to manually download the latest dfu-util and replace the executables on my machine. A helpful command to in the command line to know where to drop those files is where dfu-util and it will return the directory you need.
Here is the order of commands I did that lead to the Meadow working for me:
meadow download os
meadow device info -s COM4
meadow flash os -s COM4
meadow mono state
meadow mono update rt
meadow flash esp
Hope this helps you.
Here is the link to the first post where things started working for me:
