Ashley, I just saw this thread, and I hope you take the plunge and go all-electric. The debt free life is a good one and I totally understand your desire to pay cash for a used vehicle. Our family still uses our 2011 LEAF on long drives here and there (~240 km last Saturday, for instance), since we have access to plenty of charging infrastructure. We'd like a Tesla, but not until we're ready to buy used, for cash.
My only thought is that those Canadian prices seem pretty high, even accounting for the CAD/USD exchange rate. Would you be willing to import a used LEAF from the US? I don't know what this might cost, or whether it'd be worth the effort, but considering that 2013+ LEAFs are manufactured in Tennessee, my guess is that import duties wouldn't be a problem. Maybe you could find a good, cheap LEAF in Boston or elsewhere in New England. Getting it home could be a challenge, but that could be eased by trucking it at least to the border, or alternatively, perhaps ferrying it from New England to Nova Scotia.
Also, I'd recommend going with a 2013 or newer, with 6 kW charging (standard on the SV or SL) and ideally QC as well. You probably also want the "heat pump" heater. You might as well make those longer drives as easy as possible!
Personally, I'm working on a website (not yet released) to facilitate transactions in used EVs. Hopefully this will help people like you in the future.