Hello!
1.- Yes it is but for this you most likely will need to use custom fields to extract that information from the order and display it in the pdf. Please have in mind that custom fields are only available in the full version.
2.- I might not understand this, do you want to filter the orders by orders that have an specific product and send the pdf to them? If so unfortunately the plugin can’t do this, although bulk sending email could be added (currently it is not available but it could be added in the next release) you would also need an screen that let you filter orders by advanced terms like “Orders that have product x” which neither this plugin or woocommerce support.
We are actually working in another plugin that will let you do reports or screens like the one that (looks like) you need which will be also compatible with this plugin but that other plugin is just in the very early stage of development and i am not sure when it is going to be available =S.