Without having an example file with these issues visible, I'd like to request some sort of additional info in the help file/docs regarding certain limitations in where and when you can use specific nodes like randomize and conditional.
I have had problems trying to get conditional work with a "complex" set-up with lots of random segments in more than one "level" in a linear generator. (Levels meaning the chain of events from the generator and back to the segments). There would be randomized segments used in a sequence node, and later on several random sequence nodes in the conditional node.
I actually had problems getting the conditional node to do anything.
I'll try to make a scene file with this issue for your perusal later on.