I can't comment on how difficult or not this is. Have you been experienced this?
I use DreamHost. They are OK. When they work, all is fine and their support is generally quite good. I have had hosting issues from time to time but on the whole they have been fine. They are a budget host, just like many others who are charging that sort of price for hosting, so don't expect the fastest hosting experience compared to a more expensive host that offers VPS.
Have had experiencing with transferring. Have a lot of clients who we have transferred over from DH. Everything has to be done manually, which is a little bit of a pain. If something were to happen to your account, you couldn't take your own backup and move to a different host, for example. Where with cPanel, you just take your own backup and move around whenever you want very easily.