create an EDD download item on the Source that is a "Default" type (i.e. not a Bundle). Do not Push this to Target.
create an EDD download item on the Source site with a type of "Bundle". Add the Product created in step one to this Bundle.
Push the Bundle product to the Target. Will see an error message within the WPSS metabox stating "One of the Products in the Bundle has not yet been Syncd to the Target site."
To test: