Whatever you do, stick to Celestron or Meade. Dobsonian, Newtonian, or Cassegrain (Sch or Mak) are the way to go. Most of the little refractors (lens based, not mirror based) have serious aberration issues. I would really recommend going with as big of a Newtonian as you can afford. Meade and Celestron make some nice 90mm starter scopes for around $200.
Typically, as you add price you start to add additional features like better glass, drive motor, and hand-held controller. The controller is able (if you tell it where it) to find any object in the night sky by simply selecting the object from the menu and pressing GOTO. The drive motor, coupled with an equatorial mount, will allow you to keep the object in the viewfinder once you find it.
A killer little telescope is the Meade ETX90. With Autostar and an equatorial mount is about $450.
In his backyard, my dad has his own observatory with a Meade LX200 10" Schmidt Cassegrain, with Autostar, connected to the house Wifi and an ETX90 for traveling.