Welcome, David:
Your signals are strong and in the same direction. Trees are a problem, but your test with the C1 gives hope.
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I would love to be able to pick up channels 9 (PBS) and 11 (CW) IF POSSIBLE.
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9 and 11 are VHF-High channels; the C1 is for UHF. A VHF/UHF combo antenna should work, but no guarantee with the trees. Try a Winegaed HD7694P antenna aimed at 274 degrees magnetic on the eave mount that has the clearest path in that direction.
The CM 8-bay is primarily for UHF, real channels 14-51.
I doubt that you will need a preamp. Try one TV at the closet, then add the splitter, then see if there is enough signal at the 100 ft TV.
If there isn't enough signal for the 100 ft TV replace the splitter with a CM 3412.
Use the Roamio diagnostics screen signal strength and uncorrected errors or the TV signal strength indicator to help you.
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, but the system will not survive a direct strike.
