Speaking from someone who use to run a hosting company I can tell you, there are two great ways to do dedicated servers.
1. Managed servers are nice. You don’t have any headaches, no daily concerns. However, they are not like people think sometimes. Just because a server is managed doesn’t mean that someone is sitting there working with the machine all the time. Usually it means things like updates done for you, intrusion detection and hardening the server. But for daily bumps you’ll still need to recognize them and submit tickets for them getting fixed, then wait for a resolution.
There’s also a very wide variety of packages and interpretations of ‘managed server’. So if that’s the route you go, understand what the company’s responsibility will be.
2. Unmanaged servers are wonderful too. YOu can (and should) get a control panel which minimizes the required technical ability to manage the server. Once a server is hardened (pay a company 30 bucks or so to do this initially) and if you don’t tweak under the hood every couple days, they can and usually are very self supporting. I’ve got a personal server I use to play with sites. Not the blog and script site I run but I use it to manage about 50 websites. I haven’t had to do anything on this server for 6 months. I use automatic scheduled updates so packages are updated. The only manual thing i do is kernal updates which require reboots.
If you decide to go this rate, I HIGHLY recomend going to softlayer. They have fantastic support, great prices, and offer the best option I’ve ever seen for people wanting dedicated servers unmanaged but still want support. If you have a problem, you can pay 3.00 and their admins will manage your issue. If you’re going to be keeping things pretty simple with minimal server tweaking, my suggestion would be an unmanaged server at softlayer (get something like a small dual core machine, should be less than 200 and that includes a control panel, of which I highly recomment Plesk) and use their 3.00 admin tickets for tweaks and small fixes. If you run into big problems? hire a company (they have lists of them in their private forums) that will, for a small fee, help you.
Bottom line, managed and unamanged servers are so cheap now it’s hard to find a better way. You don’t have to mess with a virtual private server which still shared resources with other sites, and you are completely separated from everyone else. Pick up a small backup service, configure your server to do daily backups and you’re set.
Since bandwidth is dirt cheap you’ll get around 2 terabytes per month for use. Which is WAY more than you’d need unless you’ve got some really busy sites.
A server that I mentioned above could easily run 200 websites. Just make sure you get 2 gb ram and a dual core CPU and you’re set.
Just my 0.02