Pay for Sendgrid (100 / day for free is not enough) VS set up your own email server?
For own email server, do you not get flagged a lot as spam ?
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I wouldnt say that. however setting uo your own mail server is a lot of work, as you have to abide a lot of “security” rules (SPF, DKIM, DMARC, rDNS). Additionally some hosters reuire you to apply for port 25 to be unblocked (e.g. hetzner)
The set up isn’t actually hard at all, if you understand the concepts. Keeping off blacklists is the hard part, as big providers often block entire IP ranges due to one bad actor.
Edit: I meant sometimes your server gets blacklisted for something some neighboring server did