I send a huge amount of email for Cruisesheet (and am just a nut about hosting my own stuff in general), so it makes sense for me. I've had trouble in the past, but at this point I have the top reputation in both Microsoft and Google. I use a regular postfix setup with some custom stuff I've done to automatically unsubscribe people who report abuse, track engagement, automatically unsubscribe, etc. I also made an easy API so that all of my services (blog, cruisesheet, etc) can send mail easily.