I’m not persuaded this approach makes sense. When you don’t grandfather early adopters but instead migrate them to a new SKU with a discount you’ll inevitably m

I’m not persuaded this approach makes sense. When you don’t grandfather early adopters but instead migrate them to a new SKU with a discount you’ll inevitably make billing mistakes, but also, you’ll confuse people when their invoice changes from month to month even when the total charged is the same. If you just keep your initial billing logic very simple you can change it when needed as you discover what direction you want to take your business into. Having customers on legacy SKUs is only mildly annoying, and it’s not hard to segment all accounts on creation date, for instance, if you want different billing logic for legacy accounts. But you can do that after you’ve figured out what works with some experiments.