Here is how I was able to solve this issue. Although we may reach out to Microsoft for some clarification.
So our setup for the Master and Child repositories were on Server 2012 x64.
After taking Chan's suggestion to test on a different FTP client, I attempted to duplicate the test copy of the test.txt file to the appropriate directory. Upon doing that via FileZilla we received a 550 The supplied message is incomplete. The signature was not verified. Through research and other forums I was able to come across this hotfix.
https://support.microsoft.com/en-us/kb/2888853
Here is where things get a little sketchy. The download button for this KB article no longer works. It wasn't util I found this forum thread that I was able to open a link to download the hotfix. However, now that I attempt to download it again I get a Sorry, the page you requested is not available message.
https://forum.filezilla-project.org/viewtopic.php?f=2&t=27898&start=150
If you notice in the last several posts users mentioned how the Server 2012 version of this hotfix is not compatible with Server 2012 x64. We validated that this was true. But the last post by cbeerse is correct. You are able to install the Windows 8.1 RTM version.
With all the sketchy issues with the aforementioned hotfix a side, once applied, the Master Repository was able to successfully test connect and connect via SFTP. Another forum mentioned that this issue dealt with the cipher suite order. Some users found that if you placed TLS_RSA_WITH_RC4_128_SHA at the top of your cipher list the issue was resolved. This resolution has some security risks behind it so we did not test to find out if it addressed our issue.
Like I said before, we will probably reach out to Microsoft for some clarification on this hotfix to determine what kind of support there is for newer versions of Windows Server.