The Problem
1) Opened two Windows Explorer windows.
1a) First window navigate to my C:\Projects\MyProject\Bin\Release folder where "myassembly.dll" lives.
1b) Second window connected to remote machine via:  \\RemoteMachine\C$\Windows\Assembly

2) On second window, right click and select to uninstall assembly "myassembly.dll".
3) On first window drag "myassembly.dll" to remote machine window seemingly placing assembly in GAC.
4) Test my code and see that latest changes aren't showing up.

This is the short version of what happened on my end, long version is that I repeated steps 1 - 4 about 15 times throughout the day until I finally realized that I was never reinstalling my assembly in the GAC.  In actuality I was never uninstalling the assembly even though the 2nd Windows Explorer window pointing to the remote machine's GAC made it look like I was.  

To verify it wasn't working I RDCed to the remote machine and looked in the GAC after seemingly uninstalling the assembly, and to my shock I had not been.

Anyway, lesson learned is that this needed to be done via RDC and not through a remotely connected windows explorer!