check out this plugin or read through the custom calendar forum thread
You can use this to create a function or workflow so that when the first order is created, the user can select how frequently they want the order placed, or on what day of the week etc.
They can and will also need to set a date range, starting on and ending on what date.
The plugin creates a list of dates that would follow the logic you put into it.
For example Every Monday from Jan 1 to Dec 31 will get a list of dates that is for every monday of that year.
Then what you could do is create a data type that is “saved orders” where you save all the information regarding products etc that they ordered. On that data type have a data field that is a list of dates.
Then you can set up an admin page for the user to go to where they can review/edit all upcoming orders…
You would be able to display in an R.G. the list of dates with corresponding data for the order…then create functionality that they click on the date to edit the order if wished, cancel or “place” order.
If you want it to be placed automatically, you need to upgrade account and get an ability to use API workflows or recurring events.
However, if you want to be on hobby plan, what I mentioned should suffice, although no automatic orders…unless you schedule a custom event when the page is loaded, but that requires expecting that everyday somebody will log in…
I think ultimately for what you want to do, upgrading to a paid plan is necessary