Yes you will get it easily, actually "not too far into Canada" extends a loonng way in. He was evasive because receiving US satellite TV in Canada is unlawful, thus he would not make any commitment on behalf of Dish, although for many years it was in a very gray area, and it still is nearly impossible to enforce, I would imagine. I wonder each time I see the number of Dish/Direct and "Unknown" brands of dishes mounted in full view on buildings around here!!
Whether or not you will receive "local channels" will depend on what you mean by "local". Most local channel broadcasts in USA are spot beamed and thus limited to about 200 miles from their intended local area. You can always call Dish to change the service address to one near the closest big city on the US side, not mentioning your real location, and thus not raise any suspicions. I think this can be done by "chat" on the internet too.
As an FYI: In Canada, we cannot legally subscribe to either Dish or Direct with a Canadian address. For travellers like you, there should be no problem. Legally there are only two satellite companies we can subscribe to, Bell Expressvue and Shaw. ExpressVue's signal no longer extends more than about 200 miles below the border, Shaw's signal still extends a bit further. Their programming is basically from the USA along with Canadian content.
On another thread, I saw you "left your gun at home"!!! Good boy!!
Welcome to Canada and have a wonderful trip!!