Currently work shops can have two kinds of orders 'singleton' orders which are done once and then removed from the list and 'repeat' orders (created by pressing 'r') which are repeated forever or until resources run out at which point they are removed.
Firstly add quantity to all the singleton orders, this would be done by pressing '+' for a singleton order which would put a counter at the front of the Order line like so "X/Y Barrel" X being the current count of production and Y the goal. Pressing +/- changes the goal quantity allowing easy increase/decrease partway through production. When the complete these multi orders clear themselves from the list just like singletons.
Second add a new 'monthly' order option activated by pressing 'm', monthly order status is mutually exclusive with repeat so you see an M in place of the R. Monthly orders can be multi or singleton and do not clear themselves upon completion, instead they darken or get a check mark to indicate their done for the month, at the start of the new month they turn back on and the queue processes them from top to bottom. Monthly and repeat orders can be mixed but any monthly order below a repeat order will never be executed (as would any singleton order in the current system which should be indicated somehow). Monthly orders with quantity can be increased and decreased with +/- and increasing the quantity will un-check the items completion for the month if it had already been completed so the new order will go right into production if its higher on the list then the current task/
Lastly a 'loop' option activated with 'l', Loop is again mutually exclusive with monthly and repeat. Loop is similar to repeat but more flexible, loop orders have quantities like singletons but don't clear themselves when done. If any loop orders are present the queue atuomaticaly loops back to the begining upon reaching the bottom and the loop orders get processed again and again in order. Loop orders can be mixed with singletons and monthly orders without the issue that repeat causes, In fact loop might be able to replace repeat entirely.
I think this would be a far more flexible and useful system then what currently exists, one could produce some very nuanced commands like "1 bed (monthly), 1 bin (loop), 2 barrel (loop)" to get a steady production of several items in a desired ratio.