WARNING: I strongly suggest anyone using any of the default Twine 1.4.2 story formats (generally called the Vanilla formats) to switch over to using one of the SugarCube (preferably 2.x but 1.x if necessary) instead.
The reason I strongly suggest this is because the Vanilla formats haven't been updated since mid 2014, and they contain known bugs as well as code that is no longer fully compatible with Modern web-browsers.
I believe that the PassageReady special passage only relates to the SugarCube story format, and isn't a feature of the Sugarcane story format.
By default conditional based code (like <<if>> macros) within either a Standard Passage or a Special Passage (like PassageReady) only gets executed during the process (known as Passage Rendering) that displays the contents of a Passage. This means that changing the value of a variable after that process has finished will not automatically cause the conditional based code to be executed again.
So if your variable changing event based code is executed either before or during the Passage Rendering process then code within either the Passage (or the PassageReady special passage) will be effected by it, however if that event based code is executed after the Passage Rendering process then it will not effect the conditional based code.
Similarly if your variable changing links cause a passage transition (moving for one Passage to another) then then any conditional based code within the next Passage (or a related PassageReady special passage) will be effected, if on the other hand the link does not cause a passage transition then the conditional based code within the current passage (or a related PassageReady special passage) will not be effected.
If you continue to use Sugarcane then you could replace the existing <<set>> macros that are decreasing the value of $counter with a customer macro that does that decreasing for you. This custom macro could also check the variable's resulting value and redirect the player to the randomly chosen Passage as required.
NOTE: you would employ the same technique if you were using SugarCube.
So the question to you is will you be staying with Sugarcane or migrating to SugarCube? and if to SugarCube then which series (2.x or 1.x)?
I ask so that I don't have to create three different examples of the relevant customer macro.