Bob,
Since you will not be very far north of the USA border, you should not have any problem receiving Dish Network channels with your Winegard antenna assuming that you can see the southern sky. The last time I was in that area, there was either a mountain or very big trees that blocked my signal at about half of my stops.
When it comes to data through T Mobile, I do not know who they partner with in Canada, but I doubt that you will have any luck there. You will need to check will T Mobile to see if your data plan is good in Canada without a very high surcharge, and if so, what is the coverage areas.
Gerald