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My assumption is that the long length to get to the 1st story TV causes the signal strength to attenuate so much that it loses channels.
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That sounds correct. Try a Channel Master 3410 just before the splitter in the junction box. How many splits in the existing splitter? The 3410 has only one output, so an alternative would be a 3412 which is a distribution amp and a 2-way splitter combined.
If you need a 3-way split, you can use a 3412 and a 2-way splitter which would allow more signal to the longest run, and less to nearby TVs. If one of your TVs has a signal strength indicator, you can determine how strong a signal must be for reliable reception.