We have the Chat plugin for open ended discussion between workers and operators. You can see more information on this at our blog post for the plugin: http://gpsgate.com/blogComment/chat_plugin
We currently have limited event rule expressions for the Dispatch plugin but it is something we can bear in mind for future development. We are likely to introduce features centred around the time property of jobs in the future. Possible candidates are things like job and route scheduling, scheduled dispatching of jobs and routes and alerts based on the completion time of jobs.
You are able to track how well workers adhere to your routes in the software today by creating a Route Geofence (more information here: http://gpsgate.com/blogComment/route_geofence
) around your route and using the Geofence related event rule expressions.