If money is not an object and you don't mind having a scanner that's a little "different", the Home Patrol from Uniden is the current ultimate scanner, IMO. If you're used to scanners with acutal keypads and being able to tune in to frequencies manually in a quick fashion, it may not be for you. On the other hand, it is literally designed around the newbie's learning curve, and with the optional $100 "Extreme Upgrade" has some stupendous features.
Whatever you choose pretty much has to be able to do P25 digital if you want it to be useful for more than about half a year. As said above, the province is creating a new radio system which is going to be digital and 700 MHz, so getting an analog only scanner or one that doesn't do 700 will be pointless.
Look up the GRE PSR-500/600 (500 is a handheld and 600 a base/mobile), Uniden 396XT/996XT (again, handheld and base/mobile in that order), and HomePatrol here in the RadioReference wiki (look up top of the screen for the wiki link). It depends a lot less on what you want to listen to these days and more on what you want to do with the scanner. If you want to carry it around with you, the 500 or 396 is a good buy. The HP is a bit bigger than a handheld and doesn't work exactly well as a hand-carried radio, but is great for both stationary (base/home use) and mobile (in-car/truck use).
Radio Shack sells versions of the GRE radios as "PRO" series radios. I don't know what the exact numbers are - I think the PRO106 is the functional equivalent of the PSR500. The wiki page will tell you which is which. The Source (what we have now in place of RS) may sell the Radio Shack radios, and may even have Uniden radios too. I wouldn't buy from a Canadian retailer though unless it's your absolute last resort, because even with brokerage and GST fees, buying from an American mail-order company will almost always be cheaper than the price the Canadian shops are selling for.
