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ccr,
First, let's get the simple questions out of the way.
Yes, you can reverse a Splittler and feed two signals into it, and out to your equipment. Assuming it's a good Splitter. Sometimes you find ones that block signals intentionally. Yours should be 5-1000Mhz/-3.5dBm through it.
In Attic mounted Antennas, there is some singnal loss due to the Shingles, but, it still is possible to get a good signal through them. Personal experience on that issue, I have an Attic Mount and get great reception. But, you will get better reception with an outside Mount.
On hooking up the 4 TV's, that's about it, and it's not uncommon.
Now, you do have several pieces of equipment inline there, and given that, it's a lot to try to diagnose all at once.
I'd get the Amp and Splitters out of circuit for a test, and try running the Antenna directly to the DtA Box, then to a TV. Do a Search and see if you can pick up the Digital, regardless of quality as just a start. Try both Antennas that way, just to make sure that the simplest path is working.
You'll probably need a couple or more "Couplings/Unions", where you can take (bypass) the Amp and Splitters out of circuit for this test. (they're cheep)
Give that a try, and let me know how that goes, and we'll go from there.
Have a good Day !
S.W.
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