After hearing about Dangerous Prototype's search&move to a new hosting provider, we thought we'd post up about our hosting experiences!
We push over a terabyte a month, running our shop, hosting files, videos and tutorials and it's been pretty much flawless. We started with the low cost VPS service and did that for a few years, now we have a dedicated server and it's managed to live through many 'slashdottings' with no problems. We're still wary of 'cloud' services - our needs are pretty consistant so we'd rather have a single server that can provide for our needs. If our traffic increases dramatically we may move to a cloud service for image or video caching, we've done that before when were were on a constrained provider and that helped us keep transfer costs down.
When we were younger, we enjoyed running linux boxes and installing server software on every kind of hardware under the sun. However, nowadays, we like to do hardware design and let someone else manage our servers. If you're a gung-ho sysadmin type you may want a simpler setup where you are fully responsible for any software installation, administration, etc.
We also didn't want to have to deal with getting a T1 installed or administrating a router. When you have off-site hosting you don't have to worry about upgrade-paths because it's all ready set up for you.