Using fastmail atm, but going to migrate to my server eventually (because I like to tinker with servers in my spare time). I'm using mail mostly to receive email, so sending mail reliably is not a priority for me.
That said, I used to host my mail server for a while and my mail always went to Gmail inboxes. My recipients don't use some exotic providers like outlook or yahoo, so it was pretty smoooth for me. I know that people have issues with self-hosting mail, so may be it was just luck for me.
My opinion is that as long as you correctly configured stuff on your side, it boils down to IP history and reputation. So buy VPS from some expensive provider in a reputable country (so spammers are unlikely to host in this provider), ensure that received IP is clean (and its subnet is clean), set up DNS, keep it running for few months and it should be good.
That said, I used to host my mail server for a while and my mail always went to Gmail inboxes. My recipients don't use some exotic providers like outlook or yahoo, so it was pretty smoooth for me. I know that people have issues with self-hosting mail, so may be it was just luck for me.
My opinion is that as long as you correctly configured stuff on your side, it boils down to IP history and reputation. So buy VPS from some expensive provider in a reputable country (so spammers are unlikely to host in this provider), ensure that received IP is clean (and its subnet is clean), set up DNS, keep it running for few months and it should be good.