Subscription billing adds a whole layer of complexity to standard payment processing. You'll need a solid billing engine that can handle various subscription models, proration, upgrades, downgrades, and cancellations. Failed payment handling is crucial - a good retry strategy with smart timing can recover a significant percentage of failed charges. For multi-gateway support, you'll want an abstraction layer so you're not locked into one provider's API. Also consider PCI compliance implications - storing payment methods for recurring billing requires Level 1 certification if you're doing it yourself. Many companies underestimate the ongoing maintenance required for payment systems too.