> I mostly just shrug if some big advertising/surveillance company's email system won't deliver my mail, I just won't email that person.
Because that changes the tone of the opening paragraphs significantly:
> Luckily, running your own mail server is not as daunting as many would have you believe.
Sure, if you can afford to shrug off deliverability issues to major e-mail providers. Then it is, I daresay, a walk in the park!
Still, usually when sending emails to Gmail & Hotmail my emails are "lost" (they don't even appear in the spam-inbox of the receivers).
My usual workaround used to be to 1) login into my throwaway-account on their Gmail/Hotmail systems 2) send an email to my domain 3) reply to that email. After that usually my emails got accepted by those service providers, at least for a while.
I admit that nowadays I don't even do that anymore - when I see a Gmail/Hotmail recipient I just ask for another email address at a different provider or I send the email using my provider's system.
No idea if that's still the case, though.
I have never had this issue. Generally the issue is either IP reputation of your server (common with VPS providers if you get a recycled IP of a previous spammer) or your domain name.
Otherwise you are probably just unlucky enough to tickle the spam-prevention mechanisms in the almighty "algorithm" run by $BIGMAILER.
I keep one "normie" email address at a $BIGMAILER for situations like this, but at this point in my life I mostly just shrug if some big advertising/surveillance company's email system won't deliver my mail, I just won't email that person.
Be the change you want to see and all that.