Ask HN: The middle ground for email self-hosting?

> would my custom domain be free from being marked by spam?

The receipient's mail service gets to choose if it thinks your email is spam, this will happen whatever your sending arrangements, outlook is not immune from sending spam and is no magic guarantee others will give it a free pass somehow.

Recipients score your email on a variety of characteristics, many of which are under your control. A major consideration is the sending netblock, eg, residential ADSL blocks are likely to be rejected or scored to hell. Garbage netblocks like linode with a terrible reputation likewise. A clean (no history of spamming) IP in a clean (reputable) netblock will be scored higher. You can look up sender reputations here, which is the service the big email providers use.

https://senderscore.org/

So to send your own mail, you should rent a dedicated server on your own IP, you can do this for $30/mo or so. All you need to run there is postfix + SASL auth to forward your (and only your) emails.

Then you must configure DKIM etc correctly and check your emails are validly signed, DKIM requires being able to add TXT fields to your DNS.

It's very possible to do this yourself securely after a bit of a learning curve and have it require minimal ongoing maintenance.

Doesn't solve privacy, data ownership, nor google lock-in issue (but at least if I lost my gmail, I can move to a real email selfhost solution and keep my address). As my need is just to have custom domain address for the cool factor of it, this simple setup works flawlessly.

We have had this setup for several years. It is not difficult to setup, emails are delivered reliably, and email delivery cost is negligible.

Some of our users use Outlook / Thunderbird / Apple Mail as a client, some use GMail as a client (check external mail / send as user) and some use Rainloop which I set up on the mail server.