I tried self hosting. And even with SPF and DKIM set up correctly my e-mails to Outlook.com (and assocciated other domains) was just dropped. It didn't go to the spam folder, it was just silently dropped. At the time I heard that this was essentially expected behavior for an IP without a good enough trust record. This even happened when I replied to mail sent from an Outlook.com account. Having my e-mail randomly not reach its intended recipient was and is still unacceptable to me, so I bit the bullet and paid for hosting on my own ___domain. And while I'm still not happy about paying for hosting that I have sufficient capacity for on my own servers, I have otherwise been happy with it "just working".
If there’s one thing I want an antitrust investigation to focus on, it’s the gradual monopoly that Google/Microsoft/etc have inadvertently built over “clean” IP addresses. It’s now practically impossible for independents and small businesses to run their own mail servers.
I’m not blaming Google/etc for it, but it is a situation that requires a fix.
