You really have to be a glutton for punishment hosting your own email server, unless you relay it through Google or another provider. I have found getting emails through to people's inbox is hit or miss. Very difficult to avoid the spam folder. Google has monopolized the inbox and doesn't play well with little known self hosted servers. Reverse DNS, Dkim, and spf records help to a large degree. Curious to know more about the system you have setup
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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.