SpecWatchr is simply a file watcher that executes rake tasks in a Rakefile. Using DebuggerShim.cs (decorated with NUnit's TestFixture attribute), you should be able to create a rake task that will run that specific test through dotCover.
Link to DebuggerShim.cs: https://github.com/mattflo/NSpec/blob/master/NSpecSpecs/DebuggerShim.cs
And then you can change SpecWatchr to run dotCover if DebuggerShim.cs is changed: https://github.com/amirrajan/SpecWatchr/blob/master/dotnet.watchr.rb#L223
Rake file execution in SpecWatchr: https://github.com/amirrajan/SpecWatchr/blob/master/dotnet.watchr.rb#L177
Feel free to reach out to me on twitter, I'd be happy to set up a Skype session to walk you through it.
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