I've been running my Visual Studio 2010 remote debugger as a service for a while now and found the experience to be generally seamless. Every so often, however, things go pear-shaped and Visual Studio throws up it arms when attempting to connect to the remote machine:
Unable to connect to the Microsoft Visual Studio Remote Debugging Monitor named 'my-dev-env'. Invalid access to memory location.
I've found the only way to correct this is by restarting Visual Studio.