When I am sending? Well, once things are set up properly I’m pretty confident that things arrive (though nobody can ever be 100% sure of course). I also tend to mail to the same recipient domains a lot, like for work and hobby projects, so once those are tested you get pretty confident.
Unnoticed downtime is usually quickly noticed, I depend on my server for a lot of things. Senders are often resilient enough to keep things in their queue and try a few times. There’s also a fallback MX registry at my (3rd party) DNS host which will queue stuff in case the primary MX goes down.
Yep, people are enthusiastic about self hosting and like talking about what they host :)