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I think there's a lot of FUD around this. Yes, deliverability can be a PITA, but with a clean IP and good setup it's usually solvable. Worst case, you can pay a small amount to use a 3rd party SMTP relay and still get most of the benefits of selfhosting. It wasn't deliverability that made me stop selfhosting it was spam, and it wasn't that dealing with spam was that hard, it was just annoying.
As an anecdote -- I have been sitting on an elastic IP at AWS for years, with reverse DNS configured properly for it. Way early on (years ago), some spam filters would block the whole netblock, but I can't remember the last time the IP Block was wholesale blocked. I think AWS is very much on top of any spam complaints from their Elastic IPs, and as long as you don't abuse your specific IP, you are in good shape for light volume, non-spam mail.
I use Mail-in-a-Box (planning to move to ISPMail though) and i rarely have deliverability issues. My main issue is actually that the grey filter takes too long for my preferences! With self hosting mail, i consider that a good issue to have