Thanks for the reply... Yes you got the set up right! I thought it was a lot of cable... maybe a 25 footer through the basement will do it, but I don't think so.
I am using it fine right now by eliminating the second wall plate and plugging the 50' hdmi through a floor brush plate directly to the mini display port/hdmi adapter.
It seems that the last short run of hdmi from the second wall plate to the adapter was the problem.
I really hate the set up that IS working because the basement 50' hdmi is really thick and unwieldy, but until I find another short hdmi to hdmi that works, or like you said, shorten the basement run and switch out for a Redmere, it'll have to do!.