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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.