[LinuxBender]

Do you know some magic incantation for staying off the naughty lists?

Not magic, but when I managed outgoing Postfix servers for a few companies I had to set rate limits for yahoo.com an a couple other domains to reduce concurrency or they would block one of the SNAT's for a while. It probably sounds tedious but it really wasn't. There were not many MX that were as strict as Yahoo. I never ran into issues with Gmail but I think they cut some slack for corporate IP addresses and domain names.

For my own personal email servers I never had issues because I never sent at a rate that anyone cared about. The closest I got to that was running a forum that would email when threads would get updated and people subscribed to them but my solution there was to suggest to the people on the forum not to do that.