I think you worried too much about giving people a discounted upgrade price, trying to do so with Apple’s crummy bundle. Why not charge existing users the full price? It’s not like you’re actually charging all that much in the first place.
When I worked in sales and went through Force Management training we were taught to be wary of jumping to discounts. In the sales process it’s better to find customers where your product has a great fit where it’s solving their business problem very well (and for you as the salesperson to prove that value).
The type of customers you need to offer discounts to are the ones where your product isn’t solving enough of their business problem and therefore they need a lower price. Not only have you given up profit margin but you’ve also taken on a customer who will need more assistance and be less satisfied since your product isn’t perfect for them.
Obviously enterprise selling isn’t the App Store but I think it’s still good advice to think about. If you charge existing users $10 for the whole new version, the people who love the app will buy it. If you charge them $3, that means 1 of your really dedicated customers are worth more than 3 of your customers who are just buying because of the discount.
Finally, like you said, you see why developers go with subscriptions. You said you hate them, but you also want to charge your users more money. I’m not sure that it makes sense to want things both ways, at least on Apple’s platform. If it were me, I would probably embrace it. I think you can come up with something fair that is behind a subscription. Also, your royalty rate to Apple goes down by HALF for year two and beyond of a subscription. That’s a benefit I wouldn’t pass up.
I think it's quite reasonable to want to offer upgrade pricing, especially to customers who recently purchased the old version. It's just good business to ensure your recent customers don't feel screwed over having to pay full price for the new version when they just paid full price for the previous version.
The issue here is the inflexibility of the App Store, coupled with the inability to handle payments and licensing separate from the App Store. While this tends not to be much of an issue on macOS (due to macOS allowing installing applications from sources other than the Mac App Store), it very much is on iOS as well as in cases like this (as Apple has restrictions on certain kinds of Safari Extensions being distributed outside of the Mac App Store).
As a customer who purchased the StopTheMadness Link Unshortener Bundle about one and a half years ago (and therefore missed out on the upgrade pricing, while other customers who purchased StopTheMadness years earlier received upgrade pricing), I do feel screwed over. Not by the app developer of course, but by Apple.
When I worked in sales and went through Force Management training we were taught to be wary of jumping to discounts. In the sales process it’s better to find customers where your product has a great fit where it’s solving their business problem very well (and for you as the salesperson to prove that value).
The type of customers you need to offer discounts to are the ones where your product isn’t solving enough of their business problem and therefore they need a lower price. Not only have you given up profit margin but you’ve also taken on a customer who will need more assistance and be less satisfied since your product isn’t perfect for them.
Obviously enterprise selling isn’t the App Store but I think it’s still good advice to think about. If you charge existing users $10 for the whole new version, the people who love the app will buy it. If you charge them $3, that means 1 of your really dedicated customers are worth more than 3 of your customers who are just buying because of the discount.
Finally, like you said, you see why developers go with subscriptions. You said you hate them, but you also want to charge your users more money. I’m not sure that it makes sense to want things both ways, at least on Apple’s platform. If it were me, I would probably embrace it. I think you can come up with something fair that is behind a subscription. Also, your royalty rate to Apple goes down by HALF for year two and beyond of a subscription. That’s a benefit I wouldn’t pass up.