Also, email reputation and deliverability only applies to sending email. While many of the advantages of self hosting only require receiving email - eg better control over your root of trust for account auth, different address per account to avoid your email address being used as a join key for cross-company surveillance, etc. Self hosting doesn't need to be an "all or nothing" affair. Set up your domain with whatever server setup you think you'd like and start switching account identities over to that. Then only after you've gotten comfortable running it and tested deliverability, start switching over your personal correspondence.
Utilizing fancy gTLDs can still prevent you from receiving mail. Not due to a decision to explicitly block it but because it doesn’t match whatever regular expression they use to validate. Notably, .email fails consistently due to it being >3 characters. I tried to convert to using first@last.email and there is a significant minority of sites that didn’t allow it.
Good point! That's still kind of orthogonal to deliverability though. In fact in line with my point, you're better off finding this out before you start transferring personal correspondence to that domain.
The only similar problem I've experienced is sometimes companies will get uppity if you put their company name in the email address you give them. But it's easy enough to just make up a difference nonce for those cases (or start your scheme based on opaque nonces for everyone). I'm still waiting for the other shoe to drop and surveillance companies to start discriminating against non-surveillance-company email addresses the way they do against VOIP phone numbers.
I've been using gTLDs for an email for several years now (about the time gTLDs came out). It was really rough going for a while but these last couple of years it's been rare for me to have an issue.
