Ok, I've answered at least part of my own questions. I got a hold of Harmony support (only because I purchased a Harmony product in the last 60 days). They confirmed that the RF Wireless Extender does not have a mode that will output to an 3.5 mono IR jack. So as expected that is not an option. I have a call into a Xantech distributor. I explained my situation and he promised to do some research and call me back. I'll let you know what I find out.