I'm sure it would be fine, but the tower would be directly on the flight path. The truck stop location is 3,400ft elevation, and the Calgary Herald location (which is also on the flight path is 3520ft, plus another 50 or so feet for the building. In theory you should be able to add something 270ft just to get to the same height as the Calgary Herald building.
If there's anyone here with pilot experience they can chime in, but I.guessing the issue might be more to do with the ground level. If you're flying in fog and relying on instruments you might think you have lots of clearance at 300 feet above the ground until a highrise pops up.