For anyone having the same issue in future Google Searches, this si how you fix the issue.

If you want to be like me and use both EchoStation as an Announcement Machine and Simplex 2.2.3 for the Simplex Repeater Software, you must right-click on your speaker icon and select "Recording Devices". Left-Click your mic (Signalink USB or Whatever You Use) and click "Properties". Click the "Levels" Tab and drag it to 50. Select the "Advanced" tab and make sure "Allow applications to take exclusive control of this device". This should uncheck the second tick box also. Hit "Apple" and "Ok".

What the computer would do is bump the audio up to where it was feedback into the Speaker (Signalink).

Enjoy!