Hi @rosetreats. Currently this functionality does not exist. Square has something called Subscriptions that is very close to what you want, but it is missing that tracking piece you mentioned. I can assure you that I, and many others, have submitted feedback about the need for this, but since I am not Square I can not tell you if that is being worked on, yet.
If you need this now, I’d recommend heading over to the Square App Marketplace and searching for third-party subscription apps that integrate with Square. I am currently looking at one called Submatic that I think might work for my similar needs if Square hasn’t added this capability by the time I open for my 2024 season in March.
