Hi @Doran I realize this post is a bit old but in case you're still looking for a way to manage this please let me know.
My name is Dan I've worked in point of sale and payments for 7+ years and developed a software to help retail businesses leverage subscriptions. It's called Submatic (https://www.submatic.io/).
We have an integration with Square that automates member discounts/benefits based on the rules that you configure. For example you can create a membership for a product or which entitles the member to a discount. Our software tracks and communicates the membership benefits with Square so that you don't have to track anything manually.
If you're interested in getting more info or checking out a trial let me know. You can send me a direct message here on the forum, just hover your mouse over my username and then click "Send Message". Thanks!
