I think DO is really good about policing their IP space. When I signed up for the Microsoft JMRP [0], DO was already a contact of record for the IP I was using. I just appended myself to the list to get any abuse reports as well.
>Every time I read comments about the impracticality of self-hosted email, I scratch my head. Maybe I’ve just been lucky.
I feel the same. I've had one or two hiccups but smooth sailing for the most part. I'm also happy to provide receipts that show how the recipient's mail server is responding when I send the emails. It's a powerful tool to say, "your mail provider is misbehaving, look!" They will wonder how many people tried to send them email that didn't get to them.
[0]: https://postmaster.live.com/snds/JMRP.aspx