Recently had a simple sample not work right and had to iron out some things i had forgotten:
Reminder if you've only installed 64bit remote debug tools you need to build 64bit binary for remote deployment.
Also, to get remote access to mount a shared drive you have to enable sharing and do a trial run with Remote Desktop both directions just to make sure the systems can see each other.
Randomly had a 'hello world' build from one of the Visual Studio wizards refuse to let me set a breakpoint. Creating an empty project (no files, no .pch, etc.) I got things to work.