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Hi Damian Dauti,
Thank you for your interest in our plugin.
Unfortunately something like this is not possible with our plugin at the moment since we don't have subscription option. We are currently working on the packages option that will allow admin to create package of services or appointments and then customer can choose a package and book just the first appointment from it or book all, which means that will be able to create package of 10 bookings or something similar but it will not have monthly subscription or option to remind customer that all appointments from the package have past (for now).
In the future we plan to work on membership/subscription option as well but I must say that this will not come so fast since we have some other features prioritized for the first few large updates.
Best regards.