To Move or Not to Move

When we first moved to our current location, it was because work was within walking distance.
Now that we've both moved on from that job, there's no reason to stick around. The area is rather dull and they keep jacking up our rent.
I'm convinced that we could find a cheaper place in an area that's a bit more fun, especially in the winter.
The big question is, where to?
I've been doing a lot of research on rentals within the Toronto area. My preference would be someone near a subway station, especially since I don't own a car.
There's a lot of variables floating around right now. I was approved for unemployment yesterday (Yay!), so I'm hoping to avoid renting a hole in the ground.
James is still waiting on confirmation for school funding. Should that fall through, he wants to find the absolute cheapest thing out there. This makes me a little nervous considering the cheapest things out there are cheap for a reason.
Other than that, hubby would prefer to remain here and let them continue to gouge us. But that would only be because he views moving like someone in the 1800s would view going to the dentist.
So that's our dilemma right now.
Wish us luck.