Welcome Ryan
Madison looks like the better direction if there are no trees or buildings in the signal path.
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I have a short ranch style house and one 2 story brick house right behind me that may or may not be issue.
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Which way is behind you? I would need to look at a satellite view of your house with the green signal lines to see obstructions.
You will need a UHF antenna with more gain than the ones you have mentioned and a preamp for your 2Edge signals.
Consider the Antennas Direct DB8e, 91XG, and Solid Signal HDB91X.
For preamps, consider the Antennas Direct Juice, Channel Master 7778, and the less expensive RCA TVPRAMP1R.
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Unsure on grounding block tho but will come through the bottom of the current exterior cable box into the house and follow the current cable internet coax wires.
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You can't have internet and OTA on the same coax.
If the antenna is outside, the coax shield should be grounded with a grounding block that is connected to the house electrical system ground with 10 gauge copper wire for electrical safety and to reject interference. For further compliance with the electrical code (NEC), the mast should also be grounded in a similar manner to drain any buildup of static charge which will tend to discourage a strike, but the system will not survive a direct strike.
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I'm attaching a 6ft piece of 2" galvanized exhaust pipe
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That diameter might be too big for some antennas; 1-1/4 or 1-1/2 is more common. Double check it.