So I've tried both the IR2BT and Harmony BT adapter and both give similar results.

Pressing a button that just has the up or down IR code on it. Single press, no issue.

Create a macro with an up or down, and it may or may not be sent twice.

Must be the RF->IR->BT translation.

Maybe use jumps? Any other ideas?

One other thought I had was to pick up PS3 USB IR dongle to cut out Bluetooth translation.