[habibur]

Not necessarily. Had been self hosting for decades and I move the server every two years to a new IP mostly because of server/os refresh.

Right now only hotmail bounces mail. Am using DO/Singapore. Other centers fare better.

[oblib]

Same here. I setup a new email server last month and most every big email service made it pretty easy to get whitelisted, but not Microsoft. They're a total pita to deal with. Google made it very easy.

My server is a "Mail-in-a-Box" running on a DigitalOcean VPS.

[yhager]

Same here, been hosting for over a decade now. You do need to be on top of all the latest technologies, and still some problems will arise once in a while. But all in all, it's a pretty smooth operation.