I’d suggest that when you have paying customers, and your duck tape deploy process is starting to feel risky to run during business hours, that’s a good time to

I’d suggest that when you have paying customers, and your duck tape deploy process is starting to feel risky to run during business hours, that’s a good time to do your first taking of stock. Before that point it should be the fastest thing you can wire up given your own personal tooling expertise. (I’d argue that k8s is actually lean enough to be a competitor here if you’re already an expert and you use a managed service like GKE). Your infra should be in service to some uptime/performance/DX goals. Define those (honestly!) and then you can figure out what you need to improve. In particular if no customer has ever noticed downtime, and you don’t think you’d lose business if someone hit a 30-min outage, then you probably don’t need to upgrade. Twitter was notoriously unreliable in the early days and they made it, for example.