Perhaps I should have been upfront with the third point. I was trying to convey that, in my view, getting condemned to spam is the most compelling reason to not self host mail - and it's reason enough. The other common criticisms, by comparison, aren't that strong. If you're relying on your email to work, apply for jobs, or even just send things to friends using consumer services, you either have to sacrifice self hosting, or go through a lot of effort to obtain and build IP reputation.
I think it's a shame you can't reliably self host mail without jumping through hoops around IP reputation. But it's just the reality. You can be an idealist or you can be pragmatic.
In a similar vein, I now only ever use transactional email services (SES, Sendgrid) for automated emails. The sacrifice you make with self hosting is also significant in this context.
The issue of transactional email services is a good one that I might write about sometime as well. I send out the email version of the blog using SES because I know that I would have huge deliverability problems if I sent it myself. Even so, I apologize to my Apple Person readers that Apple Mail routinely hard rejects my emails from SES and I have not been able to figure out why... it comes and goes from month to month and I haven't gotten any useful info.
In general I've found Apple Mail to be probably the most aggressive major provider in terms of rejecting at the SMTP level. Microsoft seems to virtually never do it unless there is a major problem (i.e. SPF exists and prohibits the sending mail server). Google is somewhere in between, but seems to stop SMTP hard rejecting at all once it's seen the IP in use for a couple months.
The unfortunate thing, of course, is that hard rejections at least give you feedback. When they accept the mail you still don't know if it's actually made it to an inbox.
I think it's a shame you can't reliably self host mail without jumping through hoops around IP reputation. But it's just the reality. You can be an idealist or you can be pragmatic.
In a similar vein, I now only ever use transactional email services (SES, Sendgrid) for automated emails. The sacrifice you make with self hosting is also significant in this context.