I've had my X10 gear for years, but never really got around to setting it up until recently, so I'm no expert, but here's an idea.
If you can turn on the light from the remote, and from the software console, maybe try making a simpler macro with less components... just to rule other items out.
Make a new macro that triggers on A4 (assuming you have A4 free) and put that light under it to turn on. That's it, nothing else - no time constraints, no off command, nothing. Save it, upload it to the CM15A, and now hit button A4 on your remote. If that works, then maybe it's a logic issue in the way you have your macro configured, or it's an actual bug in the macro system that only happens when you use a motion sensor, etc. At least you'll have narrowed it down some.
Also make sure you've checked the time settings on your CM15A (from AHP). If you're setting it to only run after 9 PM, but your controller things it's in a different time zone and it's only 6 PM there (EST vs. Pacific) it won't run. Course, it shouldn't show you it's running in the console either if that's the case...
If all else fails, I would quadruple check all the codes on the devices one more time.