Hi George,
If you are looking for automated email templates with this feature, there is a workaround that you can use to get to a similar end result. Create a transient task for each desired "flavor" of email that you want to send out and use whatever triggers you want to control under what conditions each transient task fires. Each transient task can have its own notifications set up, so you could have two different transient tasks that trigger when a Pay Issue Fee task dockets--one for small entity and one for large entity (bonus--you can include language in the small entity version reminding the client to inform you if they are no longer small entity).
But that only works if you are automatically sending these emails out, so maybe not a good fit for what you are wanting to do.
