You say that, but there's tons of automated attempts doing the rounds on everything directly connected to the internet; centralized providers like Cloudflare can detect and prevent these patterns, whereas you need to be on the ball yourself if you have a service directly open to the internet. Exploits are exploited quickly, and while I make no assumptions about your particular website / application, a lot cannot push an update on short notice.

You would lose your wager.

DDoS attacks are extremely common at just about any scale, even if you only have a few thousand users.

Cloudflare going down like this? Actually first time I remember it happening. There’s been downtime before but nothing so major.