I never fully figured out how to resolve this. I resorted to relying on debug messages to debug my service application which is much slower.
The problem is two-fold. On the one hand Tizen Studio rebuilds the service application and tries to publish it which conflicts with the UI application I have in the same package.
The second problem appears to be GDB related, AND THIS IS MY MAIN ISSUE. The symbols do not load for the service executable making it near impossible to debug once you attach a debugger to it. If I was more of a GDB expert I probably could figure it out.