Over the past 30 years, software development has evolved significantly, with the rise of open-source SaaS startups like Lago, which balance rapid updates and self-hosted versions to cater to enterprise needs. While cloud computing has streamlined many processes, offering self-hosting remains crucial for sensitive and deeply integrated systems like billing, as it ensures security and control, which is why some enterprises prefer this option despite the complexities involved. The challenge lies in maintaining data integrity during updates without visibility into customer instances, necessitating practices like bridge versions to prevent disruptions. Although self-hosting is resurging due to its benefits, it requires careful planning and engineering to accommodate diverse customer needs and ensure seamless migrations, highlighting the trade-offs between the speed of cloud-based updates and the stability of self-hosted environments.