With the carnival idea , I think maybe Dreamland Diner might be the only one who is close to doing it? I know around the McPhillips area they have a funky corndog place which I have not tried yet.
I'd stick with food trucks over a restaurant, I've known a few people who have opened up restaurants and it's high risk/stress, money pit, and a lot of work to keep afloat. The costs really add up quickly and the post Christmas slump kills a lot of places. At least with the food trucks you can drive in to where the customers are and during the winter months I'm assuming you would be in the States running the circuit.
In an over saturated market like Winnipeg it makes things much more difficult. If I were to do a restaurant in Winnipeg I'd 100% buy into an existing franchise, it's far more safe.