A good book should really go hand in hand with any telescope purchase. As 4x4 mentioned, you can't go wrong with Nightwatch. In fact, I'd suggest Nightwatch and a pair of binoculars to get started. It's a great way to learn the sky. Another nice thing about Nightwatch is that it does go into some detail about the different types of telescopes and what their strengths and weaknesses are.
If you're really want to buy a telescope, I'd stay away from a computerized "GOTO" scope unless you're prepared to shell out at least in the neighborhood of $500 for something like a Celestron Nexstar 4SE or Meade ETX90. These are small aperture catadioptric designs. Decent optics with GOTO and tracking but with limited light gathering power due to their small apertures. The Nexstar 6SE or 8SE would be a better way to go but it's a big price jump. They also have a bit of a learning curve and require a power source (they will run on AA batteries but not for long).
A better & cheaper way to go for beginners would be with a Newtonian reflector on a manual Dobsonian mount (commonly referred to as Dobs). There are a couple of good entry level Dobs available for ~$250 to $350 that will give you a decent amount of aperture. The Skywatcher Heritage 130mm and Orion Starblast6 are pretty good bang for the buck.
As for dealers, Michael Bandmann operates Tele-Optics here in Calgary and he won't steer you wrong. If you don't mind driving to Didsbury, then I'd recommend All-Star Telescopes. They have several scopes on display and run monthly Observer Nights where you can take a scope for a "test drive". Their next Observer Night is December 12th.
http://www.all-startelescope.com/
http://www.tele-optics.ca/