rmeakins: It says "may earn", rather than "will earn".
draco963: Yes, I am familiar with that line, as I still own my original cluebook, and double-checked. In my own experience, "may," in this instance, is another of the "piscata roseae" that Westwood was so fond of throwing at its players. Jana
always dropped Trouble. Additionally, I've re-loaded several times, even going so far as to re-load from before my first entrance into Yvel Woods, just in case the random seed for Jana is set really weirdly early (other experiential evidence shows this cannot be the case, unless only Jana herself has its info flagged so early).
This is definitely a case of the port not behaving the same as the original. My memory isn't
that bad... :/
It's not a port, it's the original, it runs on our machines through a compatibility layer called DOSBox. Random numbers aren't really so random, it's entirely likely that in this instance the spawn chance for Trouble is based on some secret number which, for whatever reason, is not changing between your various playthroughs. It happens, old RNGs suck even more than new ones.
There's a very nice savegame editor out there called Scotia (linked in the UGE thread on this forum), if you want Trouble without reverting to an even earlier save or worse going through the whole game again, you can simply add it to your inventory.