Earlier quoted context omitted.
Agreed! I've been running my own mail server for 20+ years, and I would not recommend that anybody do this on a lark. Deliverability to GMail is a huge problem for me and has been for years. I even asked friends at Google to find out what the story was. All I got back is that the mail group was so careful/paranoid it wouldn't talk to them either. I would long ago have switched over to a vendor, but I use qmail-style…
Funny. I'm somewhat new to the game but my email server has had very few problems delivering anywhere (hosting a small business' email, and personal email for the employees.) I've got spf, dkim, and dmarc. I use tls on everything. Got a static ip (linode) with rdns. I've never had a problem delivering to gmail. For a while i had problems delivering to Hotmail/outlook, but participating in some sort of junk mail repor…
Setting everything up in the first place was a massive pain in the arse, definitely not for the feint hearted (I imagine there are tools/scripts to make it much easier nowadays), but it's been almost plain sailing since.
It's very rare that I have delivery problems, maybe once every year or two, which is roughly the same as through my O365 mailboxes!
Only issue is when there is a delivery problem, there is usually nothing you can do. Some of the block lists have a procedure for removal, many don't.
But after running my own mail server for something like 15 years, I've decided I just don't want the hassle any more (even if it isn't much work), and plan to move everything to O365.