My web host for a good long while was Futurehosting. My OS was Debian 4.0 (Etch). Strike one: as of now there's still no option to upgrade to a newer version of Debian. Debian lags so much to begin with, it's really painful ify ou want to use anything released in the past two years.
I had an unmanaged VPS. I ran a bunch of funky non-standard stuff on there and it ran mostly OK. I had to upgrade to get more RAM just so SBCL would run on it, which sucked but I don't know that another host would've been any better.
The good thing about Futurehosting was that they responded very fast to tickets. The bad thing was the fact that I had ample opportunity to know this. The server would go down randomly once every month or two. I'd open a ticket saying "Hi my server is down", then things would be working again in a half hour, but why did this happen so often? I don't know. An awful lot of "failed switches". I wonder how often this happened without my knowing about it, given how often it happened in the middle of my using the server for something.
With all the hardware they were burning through I would've expected upgrades or price reductions over time, given that I was a steady customer for so long and that disk space and memory keeps becoming cheaper and cheaper in the world. But the prices always stayed the same, which was another strike.
Being hosted there was annoying but never annoying enough to switch. And migrating all of my sites and data to another server seemed like a huge pain. Momentum: the worst enemy of progress.
I moved to a new host on a whim recently: Linode. It was far less painful than I expected. Thanks to Linux and plaintext config files, it was mostly a SCP-it-all-over and tweak process. It took me one evening and a bit of time the next morning. Linode offers a lot of OSes which is also nice.
I pay less for Linode than I did at FH (and I get fewer resources at Linode, but I don't need much). Thus far I'm astonished how much faster things are running on the server. Even goofing off at a terminal, the shell is more responsive. My email loads instantly in kmail instead of lagging for a second. I never knew what I was missing. Linode's DNS control panel is also pretty braindead simple to use.
Futurehosting gets a C+ from me. It worked and my website existed, but it didn't knock my socks off. Hopefully Linode is better.