Ok, so the CM-3418 and power inserter came in today. Hooked up everything and now all channels in green on the report come in at all outlets, both up and downstairs.
Upstairs sets also now receive RC 50, which is in yellow on the report. Didn't really care about that one but I'll take it.
Antenna is still not grounded, as it has been raining here pretty much every day, but am super happy with the end results.
Thank you everyone for your help!