It does get better. I can attest, I had some initial jitters too. When I signed up back near the end of 2006 I had a giant headache in April of 2007. I was down for almost 13 full days throughout the month of April. I don't remember what the problem was, but hell, it was bad. I then had 2 minutes and 33 seconds of downtime in May, but after that, it was smooth sailing. I'm on a good server, a great cluster, and I've had 99/100% uptime since as far as I can tell.
I just transferred another domain to Dreamhost and I swear, they make everything easy as pie (or a few clicks). Maybe it's just my luck, but my experiences have been nothing but outstanding, and they take hosting seriously. No one likes downtime and everyone's more than eager to get things back to normal.
(I track my uptime through a third party which checks uptime every hour on the hour, so if I went down for a couple minutes in between, then I don't have a record of it and didn't notice it myself.)
take the time.