If the one-day-loans and the regular loans have a different itemtype you can use the system preference AllowHoldItemTypeSelection. Setting it to Allow, will set hold fulfillment to be limited to the selected itemtype. This should give you most (if not all) of the wanted behavior. See: https://bugs.koha-community.org/bugzilla3/show_bug.cgi?id=15533
Stockholm University Library sponsored the development work, and have used it in production since 2016, where we separate for instance holds on books from the text book collection (7 days) and regular loans (28 days). You may need to force the selection of itemtype when placing holds to get question 1 solved.