Canadian Costs?

Takes a long post to answer your wide ranging questions. Thee are as many rates as there are answers. Fact of life, not secretive at all. So yes, it's a good idea to go directly to the providers for answers.

 

Kind of like your location.

 

There is a thread by @haider99 that answers a lot of your questions. @gokiddogo has provided a lot of answers specific to your region. As far as authority costs and insurance, I would just go to the source, i.e., MTO and insurance agents/brokers.

 

I think you could do alright with a dry van running Ontario to surrounding states, don't get the idea of the long stuff. Rates suck for dry van long loads. I have been considering it myself honestly. For the winter months at least. I do very well in summer with my reefer. If I could do short trips all year that would suit me just fine. I do some longer stuff in winter. Keep in mind load link is expensive but very worth the money for getting work.
Who knows maybe you can even run on my authority. You must have your own trailer and parking sorted out though.

 

If you have an older truck running 3-500 km radius in Ontario ins should be around 7grand with non owned trailer coverage. You would probably double that crossing the bridge plus all the border crossing fees etc. Certain times if the year the leamington reefer guys do ok running quebec but licensing will go up also plus getting loads out of quebec as an independent might be an issue.

 

#### Quebec
Secede already