Although Shadow Boxing Day was also Super Bowl Sunday this year, I don't have TV reception at my house, so I had the whole day to spend setting up a virtual private server with not one but two hosting companies.
For the non-sysadmins out there, a virtual private server is a way to run an operating system so that it looks like you're the only one using the computer, but actually there are several other OSes on that particular piece of hardware. When you're running a data center and selling access, this is both cheaper and simpler for maintenance than maintaining a 1:1 OS to machine correspondence.
My personal domain and several for members of my family have been hosted on a server owned by a friend of mine for several years. It's been nice and reliable (1636 days uptime), but it's old enough that the software upgrade repository has gone away. /proc/cpuinfo also informs me that it's a Pentium III, the name of which brings back memories of gamers and IRC and AIM and other things from my late college years.
So I did some research on VPS packages. It looked like DreamHost had the best deal for what I needed because they included "unlimited" disk space while other offerings scale disk with other resources I don't need as much of. After reading lots of FAQ material, I created an account and started setting up the server when I discovered that DreamHost's account management is kind of painful. First, for FTP reasons I think, every account on your server must have a globally (within DreamHost) unique user ID. tstone was, of course, taken, and while I was able to get flwyd, I wasn't relishing the thought of having to remember to type a username every time I sshed in. More annoying, though, was that their account creation tool seems to require that users with sudo access and users with a website must be disjoint sets. While this makes sense if you're playing sysadmin for fun, it turns out to be really painful if you need to switch accounts every time you need to install a Ruby gem or edit an HTTP config file.
Since I was being über productive on Shadow Boxing Day, I went through the whole signup and VPS setup process again, this time with Linode. This time, I got what I was expecting: a default Linux install where I have to apt-get install and configure everything myself. And to maximize the velocity, though not with optimal direction, I did it all a third time after getting things into a weird state on initial try.
Conclusion: If you want to host a whole bunch of WordPress and phpBB sites on your own server and give your friends and family self-service options for their sites (and they can remember whatever strange user ID they end up with), DreamHost is a great VPS choice. It's also a good choice if you don't need a private server for your small site. However, if you want a Linux blank slate, DreamHost is likely to prove frustrating. They've got a 14-day free trial, so I think I'll poke around a bit more and see if I can come up with a less maddening sysadmin scheme.