Good memory! A few things:
- My comment in this thread was mainly about gmail for businesses, hence the contrast between "I'm not going to fix their problems and just tell the recipient their setup is broken" and the previous "it's doable". Other mail providers are usually no problem at all, and personal Google accounts are also better.
- For email to personal gmail accounts it seemed to be enough to send a few mails and get a good reputation. Since then (and since my previous comment), I think I've started ending up in spamboxes again, but the number of messages I send to Google is very low. It's not outright rejected, though, since I would notice that.
- I still think this part of my previous message is very true: "I don't think we should dissuade people from doing it, especially if the fact that more people doing it means that it'll be easier next time because it'll be slightly more common. Many of us are in tech and the field is a small subset of the population. Even if it's a small amount of servers setup by us, that could make a noticeable on those working at bigcorps who write the hostile receivers."
> Maybe your difficulty with Gmail's mystery filtering algorithm will warn others that depending on personal email servers for reliable outgoing email is a non-trivial endeavor.
I hope not. For what it's worth, I'm still at it and have no plans to stop hosting my own mail! I'm very happy not to share my data with a third party (the ideological part of it), but on a practical level, I also don't have a spam problem and I can be sure that email arrives. No message has ever not reached me due to spam filtering. It's also much faster than, say, Runbox, which we use at work and takes at least 30 seconds for any sign up email to arrive (too short to get coffee, too long not to be slightly annoyed). As another data point, my girlfriend switched from 1und1 to my mail server because it has some conveniences, without most of the downsides (since I manage it all for her). She hasn't had delivery issues so far.
As a related tidbit, I've also recently started blocking Google from my website. They're being a dick on the internet (not to me, it's more of a solidarity move, see https://lucb1e.com/!130) and like with email, I'm not dependent on Google so I am again in the rare position to say "no, I'm not going to play your game" to Google. I'd rather encourage others to do the same than to give up and treat both email and search results as a walled garden.