Hi,
It's actually not possible to mass print the orders.
You will have to implement a plugin for that, a mass action plugin to print the elements.
It require good PHP knowledges.
Here is a link on how to create a mass action plugin:
www.hikashop.com/support/2013-08-08-00-1...s-action-plugin.html
I have added this feature to develop in our TODO list, but we can't give a date on it's realization.
With the mass actions you can manage as many orders as you want.
Connecting to an external order management system is a good idea, but there is a lot of management systems and nobody wants to use the same, and they don't have the same way of working...
So what can be done is exporting the orders in CSV file, and then use this csv file in the external management system if it allow that.