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The answer is really yes and yes.

1. To debug from your local machine you will need to set up remote debugging on your server (see http://sdllivecontent.sdl.com/LiveContent/content/en-US/SDL_Tridion_2013/task_D76A55C77B39455C88BA8159131156AC)
2. You can either upload your DLL using the CME interface or use the upload TCMUploadAssembly.exe which comes with Tridion (this can be configured as a build event from your local machine in Visual Studio if you like to work that way (see http://sdllivecontent.sdl.com/LiveContent/content/en-US/SDL_Tridion_2013/concept_62DF7C10DF8C4690B977CD7D53124D97).

Both links above require an SDL login)