I am not finding a straight forward way to place multiple items in a bib record on hold at once, if there is a way at all. We have multiple items in the same record that we reserve for various reasons. However, we have to place them on hold, one at a time. If the system allows you to place multiple holds on items in a record, there should be a way to place them all at once. Some way to select, either with check boxes or the cart, and place them on hold. This method should also include a way to set individual notes for each hold, or set one note and duplicate to the rest.
Bug 14695 added the ability to place multiple holds on a title for a single patron, but it looks like you can't specify which of the multiple items you want on hold. I'm not sure why that is.
This currently only works in staff, but if you allow multiple holds via the circulation conditions on the same record, there is a 'Holds to place (count)' counter that you can set to pick the number of items. I am not sure why the radio buttons don't change to checkboxes - maybe because much more logic would need to be implemented to give proper feedback on impossible choices? There is a patch for the OPAC pending too, that implements the checkboxes(!) Bug 15565 - Place multiple holds at once for the same record in OPAC
Depending on client feedback, I may split out the staff interface code from Bug 15565 and submit it as a separate patch here. I think Bug 15565 suffered scope creep which has made it difficult to rebase and test.