The DTV conversion and repack have changed things considerably in a lot of cross-border situations. The one I know best, because it's so near here, is Toronto and Buffalo. There are a fair number of Toronto viewers who have turned to OTA reception in recent years to get past "simsub" so they can watch US programming without having it replaced by Canadian promos and commercials.
There are two groups of transmitter sites serving Buffalo - one on Grand Island, between Buffalo and Niagara Falls, that is closer to Toronto and puts better signals up there, and another cluster of towers in the hills south of Buffalo, 30 miles or so south, that reaches more US viewers on the southern fringe of the market at the expense of good reach into Toronto. The PBS station (heavily dependent on Canadian member dollars) and the Fox station (runs a fair amount of paid programming aimed at Canada) are on Grand Island. The ABC, NBC and CBS/CW (channel share) are all in the south hills. With a decent antenna and some height (especially south-facing balconies in all those tall apartment buildings), I know a fair number of Canadians who can watch all of them.
But it's harder than it used to be in the analog days.