I would go ahead and refund 2 months of his subscription, I would only do this through stripe (or your payment gateway) so they can see the refunds if he initia

I would go ahead and refund 2 months of his subscription, I would only do this through stripe (or your payment gateway) so they can see the refunds if he initiates a chargeback for charges. Send him a polite email that you have refunded two months which goes beyond the terms of service of 30 day refunds and thank him for trying out your app. If you can see what type of card he used you could call their customer service and try to find out how long they have to make a chargeback and then refund back to that date if it's 120 days, refunding three payments might cover it or 90 days two payments might cover it depending on how long this discussion has been going on. On the other hand if $1000 won't make or break your cash flow just refund the whole amount so he'll go on his merry way and maybe you can avoid a negative evangelist for your app. Plus chargebacks are going to cost you fees and time/hassle. Sometimes you just run in to problem clients as a consultant and SaaS owner. Good luck closing things out with him.