Personally, I didn't want to do the whole "learning curve" and pay someone to manage my servers. It is a nice chunk of change for all the servers, but being able to sleep at night is well worth the extra money.
As Acro mentioned, check WHT for specials. New specials are usually posted on Monday's, so unless you are in need of one, I would wait until Monday and shop around.
Depending on the type of site(s) you will be hosting and your needs, you could either go with a VPS or Dedicated server. If it is one site and you simply outgrew a shared/reseller hosting service, and the resource usage isn't that high, you may want to look at a managed VPS or a low end dedicated server, such as a Celeron. Some providers may even offer a custom solution to fit your needs. If you do not need as much bandwidth as they advertise, you may save $10-$20 off their advertised price.