I've heard this before, but I have my own vanity domain, a well run mail server (postfix), and I I've never had a problem. I do support DKIM, SPF, DNSSEC, and of course I don't send spam.
I have heard that newly registered domains do have a period before they are trusted.
Re:Ask HN: Self Hosted vs. Gmail / Outlook?
by mister_unknown on Thursday May 04, 2017 @04:22AM
(#14263393)
I can confirm that. It took me a while to get a sane mailserver setup, but eventually I don't have any troubles with Gmail/MS/Yahoo anymore.
I used to run my own mail server for ~7 years and never had issues. I used DKIM, SPF, etc and still do although they're problematic with mailing lists...
Postfix before, openSMTPd the last few years.
I've been running my own mail servers for quite a while and I can assure that this is total nonsense. No large email host charges a fee for mail delivery. There are some rogue antispam solutions that do so, but they are rare and only used by shady small email providers. There's even an RFC stating that charging for blacklist removal is forbidden.
You will sometimes have delivery problems, although the problem is much smaller than often painted. But they can usually be avoided if you don't send spam (many people send spam but like to call it differently - your newsletter you subscribe people that haven't asked for it is spam) and if you properly react to error messages and abuse reports.
Have implemented DMARC? Is the effort worth it?
Back in the time, I had this problem with sending emails from my private server to yahoo or microsoft (hotmail, live.com, etc...), both refusing to deliver my emails to their clients as I could be a potential evil spammer.
For the subscription fees, a few weeks ago I saw a price chart for <I don't remember which company, probably Microsoft> about how much you have to pay them depending on your situation and how many emails you plan to send to their servers. Unfortunately I didn't find this page again.
I think the best option is to go for a paid service with a good privacy policy. It will cost you a lot less in time and probably in money. Also, they will probably be more reactive than you in case of problem, and more aware about security.