I've been fighting with .NET list views for the watch window and have finally managed to get a watch class being mapped and displayed via the .NET data mapper. The Data mapper is very cool, and lets you map a class directly into a control. It also lets you add new items and will allocate/edit/delete new entries without me lifting a finger! Very neat.
I'll start on the actual watch processing tomorrow, and with any luck that'll be all that I'll need to do to implement basic watches! After that I'll need to get breakpoints working and I suspect the first version will closely follow afterwards.