Forty foot high tower, antennas atop that, assure that thing has super duper grounds.
What is your zip code and what it is you aimin at?
I fail at research for line of sight (LOS) between Indiana someplace, and Ft. Wayne/ Chicago
You're looking at two problems getting reception - you're over the radio horizon so the signals will be weak at best? Digital TV cannot tolerate signals arriving with an echo from bouncing off a reflection in analog TV multipath creates ghosting, with digital it destroys the receiver's lock on the signal.
All those antenna claims about distance really mean nothing. If there is an antenna rated at 50 miles, it simply isn't going to just quit working at 55 or 60 miles. This is sales hype to try and show who has the better antenna, but I have never seen these mileage ratings equate back to antenna gain, and that's what it's ALL about. 75 miles across the water or land from a 2k' tower is not a big deal at all depending on the gain of the receiving antenna. But what really kills all these line of sight claims over water is thermal inversion and just normal moisture in the air. One can deflect the strongest carrier completely off the ground, and the other will simply eat it up from fog or excessive humidity (moisture) in the air.
THEN, you also need to worry about the radiation patterns of the broadcasters. Unless they are all combined on a community antenna, each station that you might receive can, and probably will have a different pattern. They can pick and choose the markets they choose to hit, and even control down-tilt (distance as it were), and you may or may not be in one of them. TVFOOL is probably the easiest consumer site to analyze the criteria, but it's not gospel doe to all the weather variations
When You done building that really nice antenna and just before you put it up up then put a yagi on top of it with its' own set of downleads. You won't be sorry you did that. Ones with little motors are less than 25 bucks, sometimes much cheaper, they rotate drive off of the little cable it comes with.