I have continuously run my own email server since around 1990 in one form or another. Established a vanity domain in the mid 1990's and started hosting email on my own domain. I must say that has been a more difficult task as time has gone on and has required I be more savvy about IP reputation and how to maintain it.
Sometime last year I moved my email server from a VPS to a dedicated host and my wife began complaining over this past summer that she could no longer send email to Outlook.com and friends as well as Optonline. Given that she's a dog trainer trying to expand her client base this is pretty much a disaster for her.
I attempted to work with the ISP hosting my dedicated server and they were not interested in fixing *their* IP reputation. Seems the above mentioned providers were blocking *all* of the IPS's IP addresses out of hand. They insisted they'd have to work with the ISP and while they were sympathetic they wanted to work the issues through the ISP. There's more to that I'm sure but after my ISP frustrating me by not being responsive I talked to some new folks.
First question I asked before signing on was "how is your IP reputation?" After a lengthy explanation on how they have "high profile reputable clients" they assured me I'd have no problems. So I signed on the dotted line, installed a Puppet client on the box and set things up so the box would get configured as my mail exchanger.
During shakedown I didn't notice problems right away so I edited DNS and pointed my MX records to the new box, added my SPF and DKIM records for the new host and powered off the old box. The very next day I composed an email to someone that I communicate via email on a fairly frequent basis and after hitting "send" got a bounce notification within minutes.
Verizon was blocking the new server. New problem.
It took many attempts and iterations I finally worked out between my new ISP (who graciously gave me a second IP address for outbound email) and Verizon I finally got whitelisted.
So, yep, the Internet has become increasingly hostile to private email servers, but the problems can be worked out with some effort and tenacity.