Gen II to Gen III ???

Why would you trade it in? With gas prices going up, up, up, you could probably fetch a good, even very good price for it on the open market. With that kind of milage you could probably get $16-$18k for it (not sure what options you have). Not sure what that translates into in Canadian $$$$. I just looked at KBB on a base model.

 

You mentioned you are a happy owner of the 2007. I had to upgrade from the 2nd gen because I was miserably uncomfortable and awkward in it. But after renting the 3rd gen a bunch of times and waiting, the switch paid off. Comfort is peachy in 3rd gen.

3rd gen could use a little tweaking on the interior. I find the steering wheel slightly skewed to the left and armrests could be better fit, more padding. Steering wheel could be a skosh closer, but these are minor points.

It's a good car. It can be a bit of a pain dealing with other oversized SUV with 250 HP ... today I pulled onto an uphill ramp to freeway, pretty steep. Darn Jeep GrandCherokee didn't want to go around, lane merge, I ended up infront going up ramp.
I gave it quite a bit of gas, but could see the knucklehead behind with head in hands, raring to go and blow away gas. I wasn't going that slow, really. HSI power zone was full.

Still, sort of a drag we have to put up with other traffic that are frankly sporting too much excess power and getting 20 MPG at the pump.

 

I think that Cherokee would be lucky to get 20 mpg. My Wrangler on a good day is at 18

 

Constantly trading in cars is a good way not to save money. If you're tired of your Prius chances are you'll get tired of the next one. So I would just trade it for a car you REALLY want to drive and not look back. Of course I'm making one big assumption based off of not having any other info from you.