Something like this would have to be implemented in core I think because the bindings do not really have access to Items in OH 2.x+ architecture. That’s why Expire was moved into core.
Ideally, this should be built into the add-on because retrying isn’t really applicable to all technologies.
It also gets complicated when an Item is linked to multiple channels and if profiles get involved.
This would be a great candidate for a rule template though. Put all the Items into a group, add the “retransmit” metadata to those Items and one rule can do this. Published to the marketplace, and it becomes installable like an add-on.
My Debounce [4.0.0.0;4.9.9.9] is a similar concept.
Of course, autoupdate would need to be disabled for this to be meaningful.