I have checked. "Play" behavior in Feedback is a bit confusing (even for me, as you could see in the previous post...), but that is not a bug. When "Play" is used in monitors, related Monitor preparation (so, the Actions in the Logic Control where that monitor is defined) are still executed. And in case conditions prevent that monitor (as in current case), nothing is executed.
Changing that behavior will be good in that particular case but can be even more confusing in other cases, when played actions use preparation results... I mean I don't see better solution.
Ok, I will stop with rocket science
You need to move "Time" in the "Record" definition to the top of the list. That will not change the whole logic, but will allow you to "Play" OSC in feedback (and so assign it to the control).
But your "fixed" to my definition in practice break indented sequences. Without "Transport:Rec" condition, "Command 'Stop' *" means you stop transport. Always. No record, no pre-roll. Since nothing else is ever executed. The same fro "Command 'Record' *".
These 2 commands should be executed in case you don't want pre-roll, so when you are already recording (and so want stop) or AutoPunch is not enabled (so there is no reason to pre-roll).