Hi @Winoinchief I'm not sure if you decided to go with managing this manually or went with an add-on. Currently there is not an easy way to manage a Wine Club directly in Square. You can try to manage it manually but it will get very difficult as the club grows beyond a handful of members.
I founded Submatic and we work with Wine Clubs to automate club management. Our Square integration allows for a lot of flexibility around how you manage your club and the benefits that you offer. Please check out our app in the Square Marketplace here https://squareup.com/us/en/app-marketplace/app/submatic and you're welcome to sign up for a free trial if you're interested. Thanks and please let me know if you have questions.
