Jayson Smith writes:

 > What I mean is that I'd love to find a good, reliable smarthost I
 > can direct my SMTP server on my VPS to use.

You could try some of the services listed here:
Hosting: https://wiki.list.org/COM/Mailman%20hosting%20services
Consulting: https://wiki.list.org/COM/Mailman%20consulting%20services
They might have a better idea or offer exactly the service you want.

Otherwise, I think you kinda have to move your VPS to the service you
want to use, and on top of the monthlies for running a server they'll
charge you for email volume.  AWS SES for example is 10,000 emails for
$1 billed monthly, and there's a throughput charge as well but that
too is probably negligible unless you're mailing videos.  They do
promise an IP with a clean reputation and they bonk your neighbors
(and you) automatically for sending more than a tiny amount of spam,
so I'd expect it to stay that way.  FWIW ....

 > The real problem I'm seeing is that seemingly within the last few
 > years, at least some VPS providers (Linode and Digital Ocean for
 > sure) have started getting entire IP ranges put on blocklists.

This is nothing new.  Effort-minimizing admins have been blocking
whole netblocks for well over a decade.  I think one new aspect is
that non-admins have borrowed the technique of mass-reporting to try
to shut down all aspects of an individual's or organization's Internet
presence.  I wouldn't block at the SMTP CONNECT level based on IP or
domain alone for the reasons you give for running your own smtpd, and
I doubt Google or Microsoft do.  But I know a lot of admins who do.

I don't know what to do about it.  I think my own server at my
university got on Microsoft's bad side once, but it got better fairly
quickly.  I did contact Microsoft but I don't know if it had anything
to do with getting off their blocklist, the only reply I got was a
'bot saying thank you for contacting Microsoft, check this link.  I
don't think they have their best minds working on the problem.
Instead they get customers by being too big to block, is my guess.

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