I think the standard answer is to use a smarthost.
The blacklisting shouldn't be permanent, though; my self-hosted mailserver took about a year to earn the trust of GMail. I hzave no idea how Hotmail's spam filtering works. I think they just shitcan randomly, unless it's sent from Hotmail.
I'm no longer running a self-hosted server. It's hosted by my (obscure) ISP, but it's still a custom domain. I have no deliverability problems, not even to Hotmail.
The blacklisting shouldn't be permanent, though; my self-hosted mailserver took about a year to earn the trust of GMail. I hzave no idea how Hotmail's spam filtering works. I think they just shitcan randomly, unless it's sent from Hotmail.
I'm no longer running a self-hosted server. It's hosted by my (obscure) ISP, but it's still a custom domain. I have no deliverability problems, not even to Hotmail.