Five years ago I happily procured a dedicated Red Hat server from a very popular managed hosting company (if not "the" company). I did this mostly out of convenience for my clients, who would always call me with hosting issue this or that, and there would be little I could do for them other then help create a support ticket for their existing host. It got to be a pain, especially after a major Dreamhost outage way back when, and a lot of my clients were on Dreamhost. I figured this would be a good time to look at getting my own server and selling space to my clients on it.
A lot of my clients expressed interest in more reliable hosting even if it mean more money, so I figured it was time to pounce. Soon I had my own dedicated box, and soon enough I was turning a little profit, not much, but better than nothing. Better yet it never went down (well, once, but that was a freak accident and they rebounded quickly). Better yet, the phone support was amazing, and I could easily install stuff on it and do things that made my life as a developer easier.
Life was pretty good for 5 years. Some headaches, but nothing outside the normal.
Then my 5 year contract was up. The server was ending it's life cycle, and with that, so was support for the server. It was time to upgrade ol' betsy before things got ugly.
I was floored to learn that costs had more than doubled since I signed my original contract. When I expressed my dismay, they wanted to push me into the cloud, but while that seemed to make their life easier I didn't think it would make my life easier. And it was still going to be way more expensive than ol' betsy. Upgrading betsy seemed it would cause more headache than it would solve, and she couldn't even run the latest Red Hat anyways.
On top of that, I was going to be responsible for migrating everything myself. Websites, settings, email, databases. The works. No way I had the time or inclination to do that, so I'd have to hire a 3rd party - costing yet more money.
But the really kicker is that I was not about to tell my clients that their hosting cost was more than doubling. If they bailed, I'd be stuck with a huge bill every month.
I investigated other hosts, but in the end, decided this was a headache and time suck that I never wanted to deal with again. What I needed to do was to sell the server, and ideally to a company that had phone support as I know some of my clients would really need that. And guess what? I found such a company. And a good one at that. Migrations have been going through well, clients are happy, and guess what? They are doing the migrations, not me - the weight on my shoulders is gone. And also guess what? If my clients have any issues, they pick up the phone and call this other other company, not me. I'm sure I'll still get some questions, but hey, this is a huge improvement.
So there's the scoop. If you get a dedicated server, just know time's a tickin'.